The Roommate

This contains cross dressing, non-consensual sex, gender bending/change, and sex between the protagonist and both a male and a female. If any of this bothers you, please skip this story.

*****

It's crazy how it all started. I was Leigh, a recent college graduate come to the big city to try to make a success of myself. I was short and slender for a guy, only about 5'6" and 125 pounds. But it's brains that count nowadays, not muscle, right? I had brains, all right -- even majoring in finance, but couldn't seem to come up with any good jobs.

I managed a few temp jobs, but none of those seemed to work their way to full time, and most of those didn't pay that well anyhow. In one of my temp jobs, I made friends with Carrie, who had gone to the same college as me. She had zero interest in a romantic relationship, not that I could afford to take her out anyhow.

I was struggling to pay rent with only stray temp jobs, when I hit a dry spell. Hell, rent in the city is damned expensive, and I was living in something not much up from a slum. As my cash was hitting zero and I was about to be thrown out, I ran into Carrie again. She was living in a two bedroom place that her father was underwriting for her.

Daddy really wanted Carrie to get a roommate -- female, of course -- to share the rent and relieve him from some of the expense. She told me I could stay there for a little while, as I tried to get on my feet. Separate bedrooms and separate beds only. She had no intention of making me her lover. Carrie was about my height and weight, with a cute face, b-cup boobs, and a nice ass.

At that point, I'd have about sold my soul to avoid living on the streets. As it turned out, maybe I did. I moved in Carrie's extra bedroom, assuming I'd get a job and be able to move out. The temp jobs kept coming -- not paying enough for me to get my own place, but I could cover half the food and utilities. Couldn't really contribute much to the rent, nor could I save anything toward my own place.

We sort of limped along like that for a couple of months, until Carrie came home from work one evening, very upset.

"My father is coming to town to see how I'm doing."

"That's nice."

"No, it isn't. Daddy won't like the fact that a guy is living here with me -- a guy who isn't even paying half the rent."

"What can we do?"

"You need to find another place to live for a while."

"I've looked. I've talked to people. I can't afford my own place and I can't find anyone else who'll take me in."

"I can't have a guy here when daddy arrives."

"When does he get here?"

"Tomorrow evening, and he's staying in town for a week. He has some business in town and he's checking on me while I'm here."

"What are we supposed to do?"

"You can't be here. You have to go."

"Carrie, please, I have no place to go."

Carrie looked sympathetic, but adamant. Then she paused, looked thoughtful, then looked me over carefully. That should have been a warning, but I was so upset about being thrown out, that I missed it.

"I can't have a guy living with me, but I could have another woman living with me."

"How does that help?"

"Follow me."

Carrie took my hand and led me into her bedroom and into her bathroom.

"If I can't have a guy living here, but can have a woman, and you have no place to go, then we just have to make you into a woman."

"Hell, no."

"You'd rather live on the street? Okay, take your stuff and get out."

"Isn't there anything else we can do?"

"Basically, no. What's the problem? You just have to dress as a woman for a week. Why is that a big deal?"

"You don't understand."

"You're right, I don't. I'm offering you a way to stay here and avoid having to live on the street."

"I don't have any women's clothes -- and no money to buy any."

"I've got lots of clothes, and you're about my size."

"I'm not sure I can pull this off."

"If you don't pull it off, daddy will not only pull the plug on you being here, he'll quit helping me with rent and I can't afford this place on my own. For both our sakes, you need to do this right."

"Shit. What do we need to do?"

"You need to shave off all your body hair -- underarms, back, chest, everything. That's for starters. I've got razors and depilatory cream. Get cleaned up. I'll get you some clothes."

She handed me a razor with shaving cream and some hair removal cream. She had me take off my shirt and slathered it on my back, not that I had a lot of hair there anyhow. I shaved my face again, along with my armpits, then my legs, and put the hair remover on my chest and arms. I gave it a few minutes, then showered it off. When I got out of the shower, my guy clothes were gone.

I wrapped a towel around myself and went into her bedroom, where Carrie had laid out about half a dozen outfits, along with bras and panties. She had me put on bra and panties, along with a skirt. I felt weird as shit, but I guessed it was better than living on the streets and sleeping under bridges. She padded out my bra to make it look like I had boobs.

"We'll move these clothes to your room, and hide all your boy clothes."

"So I'm stuck this way for a week?"

"Now we need to do something about your hair."

"What do you mean?"

"It's long enough, but we need to trim and style it."

"Fuck."

"No chance of that."

Carrie used a blow dryer on my hair, styling it with a brush.

"Pay attention to what I'm doing. I'm not doing your hair every day."

Once it was dry and styled, she took scissors and trimmed a bit to make it look more feminine. I was shocked when I looked in the mirror at how much like a girl I looked. Carrie handed me a cute top, which I put on and a pair of low heels, which did just barely fit. Then she sat me down and did makeup, with base, highlights, eye shadow, and lip stick, among other things. And again told me I needed to learn to do my own.

"This is only for a week. Can't you do my hair and makeup for a week?"

"No. I have a job, and don't have time to do my own makeup and hair and yours too."

Carrie gave me several pairs of shoes. I guessed it wasn't a problem, since it looked like she had more than fifty pairs in her closet. She also had a closet full of clothes, so she wouldn't exactly miss the ones she gave me. Then again, I figured she could have them back in a week, after daddy left.

"Okay, Leigh, there's an inexpensive Chinese place down the block. Let's go get some dinner."

"Sure thing. Just let me change and clean off this makeup."

"No. You're coming like that."

"Why?"

"Daddy will probably take us out to dinner a few times while he's here, so you might as well get used to it."

"I could skip the dinners with daddy."

"That would offend him. Trust me, you don't want to offend him. Not if he realizes you aren't paying any rent."

"Shit."

"And what if you get some temp assignments while he's here?"

"There's no way I'm going to a temp assignment looking like this."

"Stupid, if daddy knows you aren't paying rent, and finds out you didn't take a temp assignment that was offered, he'll get pissed."

"I can't fucking win, can I?"

"You want a place to live, you're like this for a week, both at the flat, and in public."

"I am so fucked."

"You should be so lucky."

We went to the Chinese place and Carrie paid. We sat and ate our Chinese food, and most of the time no one seemed to pay any attention to us. I looked up one time and saw a guy looking directly at me. When our eyes met, he gave me the biggest smile. I blushed, which Carrie saw, and figured out why.

"Well, Leigh honey. It looks like you have an admirer."

"Like I need that shit."

"It could be a lot worse, believe me."

I avoided looking in the direction of that guy, though it was hard to ignore his apparent interest. I thought about him every time I was about to look in that direction, and I think I blushed a couple more times. A little later, the guy walked by our table, stopped and put a business card on the table beside me.

"I'm sorry if I embarrassed you, but you're cute and if you're available some time, I'd like to take you out. Give me a call."

I sat there, totally stunned. Carrie seemed to take great pleasure in all this and looked up at him.

"Leigh is a little shy, but I'll see what I can do with her."

"Well, I hope to hear from you soon, Leigh."

The man smiled and left.

"Are you crazy? There's no way in hell I'm calling him back or going out with him."

"Got rid of him, didn't it?"

"Now he knows my name. Now he thinks I might call him."

"I'm not insisting you call him, or that you go out with him. That was just a way to make him go away happy."

We finished our meal and went back to Carrie's apartment. I was looking over my shoulder all the way, worried that he might be trying to find out where I live. Once we were inside with the door locked, I began to relax a bit.

"I need to change back to my normal clothes now."

"These are your normal clothes, until daddy is gone. I've got your boy clothes stashed away where my father won't find them."

"I don't know how I'm going to get through this."

"Better than you'd get through living on the streets."

"So what now?"

"I totally forgot to do your nails."

"My nails?"

"Nail polish, silly, on your fingernails and toenails."

"Jeez, do you have to?"

"Yes, you need to be a very proper young woman."

Carrie painted my nails, and we watched cable while they dried. Then she gave me a pink nightie, luckily not too sheer and told me to change into that. My mind was so blown at that point, I'd gone numb. I went in my bedroom, took off my skirt, bra, and top, leaving on the panties, and put on the nightie, then came back out to watch a little more before we each went to bed.

...

The next morning, Carrie took a few minutes to touch up my hair and makeup, before leaving for work. I figured I'd just hide out inside all day, when I got a call with a temp slot for the day. I didn't want to do it -- not the way I was dressed, but I had no idea what Carrie had done with my regular clothes. Besides I really needed the money. I texted Carrie that I was going to work.

I made sure my appearance was decent, then took the subway to my assignment. It was a place where I'd never worked before, so they didn't know me. That was a blessing, and they just seemed to accept that their temp was a woman named Leigh.

I damned near walked into the men's restroom at one point before I caught myself. I went in the women's room, went into a stall, latched the door and sat on the toilet. I know women sit to pee, so I did and even though I didn't need to wipe the way a woman would, I got some toilet tissue just in case anyone was listening.

They entered my time worked at the end of the day, and I headed back to the apartment. I was hoping I'd have a little time to relax from my ruse of being a woman, but when I got there, both Carrie and her father were both there. Daddy was late forties or early fifties, with a full head of hair, graying at the temples. He looked like he was still in decent shape and wore an expensive suit.

"So this is your roommate Leigh. So nice to meet you, darling. I'm happy to be able to spend time with my daughter and her lovely roommate."

"Daddy wants to take us to dinner. Take a minute to freshen up, and we'll go."

Dear old daddy insisted that I call him George. He got a taxi and took us to one of the nicer places in town. As we walked into the restaurant, George had one arm around Carrie's waist, and the other arm around my waist. I didn't care for that, but what could I do without blowing up everything. Daddy ordered a bottle of nice wine and poured us each some. After what had happened, I damned sure needed alcohol.

The first part of the evening, Carrie brought daddy up to date on what was going on. Before our meals arrived, Carrie turned to me.

"Leigh, dear, let's go to the ladies room."

I was flabbergasted, but women often go together to the restroom, and I wasn't sure I wanted to be left alone with George anyhow. As we went back Carrie spoke.

"I know you were probably in the women's restroom at that office today, but be cool."

"I have no intention of letting anyone know I'm not female."

We peed, washed our hands and touched up our makeup. I was surprised how quickly I was catching on to doing my makeup. We returned to the table, and there was another man there with George. George introduced him as Brian. Brian seemed interested in my college background and my degree in finance. He seemed pretty knowledgeable about finance, and spent some time as we ate delving into how much I knew.

Brian and I talked finance throughout dinner as George and Carrie talked about other things. We finished eating and George paid the bill, then Brian turned to George.

"You know, I think you were right about this young lady. She just might do."

I had no idea what he meant or what was going on. George filled us all in.

"Carrie told me you had been looking unsuccessfully for work for a while, only managing temp jobs. Brian owes me a favor and I asked him to talk to you and see if he could find a place for you at his company."

With that, Brian turned to me, and handed me a business card. "Be at our offices at 9 sharp tomorrow morning. I won't make any promises, but if you impress some other folks the way you impressed me, we might have a place for you."

Carrie threw her arms around me and hugged me. After months of scraping by, I might now have a chance to really get a half decent full time job. I might be able to pay my way for a change. Then it occurred to me, George and Brian both thought I was a woman. They would expect me to show up and interview as a woman. And if I got hired, I'd be hired as a woman. I wavered between reverie and shock, as George spoke.

"You seem to be a nice girl, and I know you haven't been able to carry your share. I expect you to work your ass off and begin to pay half the rent at that apartment."

"I'll do that sir. I really appreciate the opportunity."

I was stuck. Brian was a friend of George. If I screwed up, George would know and my ass would be on the street. If Brian found out I wasn't really a woman, George would find out and really be upset. I needed the job. I needed a place to stay. Now it all seemed to hinge on me continuing to appear to be a woman.

I thought I'd be dressing as a woman for a week to keep George from throwing me and possibly Carrie out. Now, at last it looked like I'd have a job, but only by continuing to dress and act like a woman. How does one manage to be both ecstatic and depressed at the same time? Well, I was finding out. And it looked like I'd be finding out for the indefinite future.

George offered a toast to me assuming I'd be hired the next day. I drained my glass of wine, and another one shortly after. All the wine started to go to my head, and when we left, I was almost staggering. George again walked out with an arm each around Carrie and I, but with me, I felt his hand slipping down over my ass.

George took us back to the apartment and walked us up there. He came in with us, and Carrie immediately hit the bathroom. When she did, George grabbed me and began to kiss me. I was drunk and my reaction time was seriously impaired, but after a bit of the kissing I pulled back.

"No. I can't... We can't... Please. Don't."

George stopped kissing me but still held me tightly against him. I was glad my panties were holding my cock in check, because I was getting a hard-on. It blew my mind that having a guy kiss me like that would make me hard, but it was happening. It scared me though, just as I was scared about what George might try to do, and how he'd react if he found I had a prick.

George held me tight for what seemed like an eternity, then gave me a quick kiss, and loosened his hold on me.

"All right, then. Get that pretty little ass to bed. I expect you to be sober and making a good showing of yourself at your interview tomorrow."

With that, he turned me around and patted my ass as he gently moved me toward my bedroom.

"Sleep well, darling."

I staggered to the bedroom, closed the door locked it, took off my skirt and top, pulled on a long tee and collapsed onto the bed. I both feared and craved George's touch, and rolled into a fetal position and cried myself to sleep.

...

I woke up the next morning, showered, did my hair and makeup, then gave Carrie a chance to tweak and critique before she left for work.

"I saw my father pawing you last night after we got back."

"I swear, I didn't encourage him."

"I told him to keep his hands off you. He seemed to think you were just playing hard to get."

"Oh God, no."

"Just make sure you get that job today. This whole thing will fall apart if you don't."

"I want a job, I just wasn't looking to be employed as a woman."

"No excuses. You have an opportunity -- take it."

I dressed as nicely as I could -- not sexy, but very business-like. I went to the company and got there a little before 9am. I told the receptionist that I was there for a job interview, and she had me take a seat in the lobby. Right at 9 o'clock, Brian came out and warmly greeted me. He ushered me back in to an office where there was a vice president waiting to interview me.

I talked with the vice president for an hour, covering what I'd studied in school, what I actually knew how to do, what kinds of jobs I'd been doing -- all the usual stuff. At the end of the hour, he seemed quite pleased and asked if I wanted anything to drink or if I needed to use the restroom. I asked for some water, and a woman brought it to me shortly after.

I waited about ten minutes before an assistant vice president came in to interview me. All the same again, plus all the usual. Where did I see myself in ten years? What did I think my strengths and weaknesses were? Why did I think I should get this job? This guy was probably a little tougher than the VP had been, but even he seemed satisfied at the end of the hour.

By then, it was almost lunchtime, so I hit the women's restroom, and was escorted to the company cafeteria by a man who worked there. We talked over lunch, and I only realized afterwards that he was my third interview and was the manager I'd report to if I were hired. After lunch, he took me to Human Resources where I met Katherine, who was manager of that function.

We had what amounted to a final interview, which again seemed to go very well. I found that Brian was a senior VP and the boss of the first VP who had interviewed me.

"Well, Leigh, you've done very well. Everyone who interviewed you felt you were qualified for the position. Beyond that, George is a very good client of this company, and he recommends you."

"You mean I'm hired?"

"I need to cover a few other things before we make an offer. First, you are a very lucky woman. This company is very accepting of LGBT employees, including transgender."

"You mean...?"

"Yes, I know you were assigned male at birth."

"Please don't tell George or Brian."

"That is strictly between you and me. But you need to understand, there will be no interoffice romances or affairs."

"No. Absolutely not."

"While we are a tolerant company, there are men here who aren't so tolerant in their personal lives. We don't want any trouble whatsoever."

"Trust me, that's the last thing I want."

"Even though you have a couple of important people backing you, we still expect you to work hard."

"I promise I will."

"Since you're being hired as a woman, you'll be expected to dress as a woman and use women's facilities."

"Yes, ma'am."

"Our medical plan does not begin until you've completed three months probation. We have made provision though. We have a small clinic in house, usually staffed by a nurse practitioner. That can be used for any medical problems until the insurance kicks in."