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The Roommate Transsexuals & Crossdressers I found that Brian was a senior VP and the boss of the first VP who had interviewed me. She had me take off my shirt and slathered it on my back, not that I had a lot of hair there anyhow. ***** "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." "Yes, you need to be a very proper young woman." "I am so fucked." "Shit. So nice to meet you, darling. I was shocked when I looked in the mirror at how much like a girl I looked. I went to the company and got there a little before 9am. I was shocked when I looked in the mirror at how much like a girl I looked. I blushed, which Carrie saw, and figured out why. We had what amounted to a final interview, which again seemed to go very well. I was drunk and my reaction time was seriously impaired, but after a bit of the kissing I pulled back. "Carrie, please, I have no place to go." We had what amounted to a final interview, which again seemed to go very well. Carrie was about my height and weight, with a cute face, b-cup boobs, and a nice ass. It's crazy how it all started. He came in with us, and Carrie immediately hit the bathroom. Now, at last it looked like I'd have a job, but only by continuing to dress and act like a woman. I've talked to people. 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. I thought about him every time I was about to look in that direction, and I think I blushed a couple more times. All the wine started to go to my head, and when we left, I was almost staggering. For both our sakes, you need to do this right." "Leigh is a little shy, but I'll see what I can do with her." "I could skip the dinners with daddy." "You're right, I don't. You have to go." "Well, I hope to hear from you soon, Leigh." "That is strictly between you and me. I needed a place to stay. When she did, George grabbed me and began to kiss me. I might be able to pay my way for a change. I've got razors and depilatory cream. He has some business in town and he's checking on me while I'm here." "You don't understand."


"Isn't there anything else we can do?" "I can't have a guy here when daddy arrives." Dear old daddy insisted that I call him George. I might be able to pay my way for a change. She had me take off my shirt and slathered it on my back, not that I had a lot of hair there anyhow. 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." ... "Leigh is a little shy, but I'll see what I can do with her." "Got rid of him, didn't it?" "No chance of that." I avoided looking in the direction of that guy, though it was hard to ignore his apparent interest. "Be at our offices at 9 sharp tomorrow morning. It was a place where I'd never worked before, so they didn't know me. Can't you do my hair and makeup for a week?" "What are we supposed to do?" Carrie gave me several pairs of shoes. I've got your boy clothes stashed away where my father won't find them." The man smiled and left. I can't afford my own place and I can't find anyone else who'll take me in." Carrie threw her arms around me and hugged me. 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. "I want a job, I just wasn't looking to be employed as a woman." "Well, I hope to hear from you soon, Leigh." I thought I'd be dressing as a woman for a week to keep George from throwing me and possibly Carrie out. I was drunk and my reaction time was seriously impaired, but after a bit of the kissing I pulled back. I avoided looking in the direction of that guy, though it was hard to ignore his apparent interest. Beyond that, George is a very good client of this company, and he recommends you." The first part of the evening, Carrie brought daddy up to date on what was going on. "You'd rather live on the street? Okay, take your stuff and get out." "Better than you'd get through living on the streets." "It's long enough, but we need to trim and style it."


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. Get cleaned up. I'm not doing your hair every day." "It could be a lot worse, believe me." "Follow me." The first part of the evening, Carrie brought daddy up to date on what was going on. I really appreciate the opportunity." "Yes, I know you were assigned male at birth." "No. He seemed pretty knowledgeable about finance, and spent some time as we ate delving into how much I knew. 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. Absolutely not." George stopped kissing me but still held me tightly against him. I've talked to people. I expect you to work your ass off and begin to pay half the rent at that apartment." "It's long enough, but we need to trim and style it." Carrie used a blow dryer on my hair, styling it with a brush. How does one manage to be both ecstatic and depressed at the same time? Well, I was finding out. Then again, I figured she could have them back in a week, after daddy left. "Basically, no. Daddy won't like the fact that a guy is living here with me -- a guy who isn't even paying half the rent." "You can't be here. Daddy won't like the fact that a guy is living here with me -- a guy who isn't even paying half the rent." I was struggling to pay rent with only stray temp jobs, when I hit a dry spell. I both feared and craved George's touch, and rolled into a fetal position and cried myself to sleep. "So I'm stuck this way for a week?" "I've got lots of clothes, and you're about my size." "Now we need to do something about your hair." "You're right, I don't. Don't." "There's no way I'm going to a temp assignment looking like this." "I swear, I didn't encourage him." 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. I've got razors and depilatory cream. I needed the job. Give me a call."


"It could be a lot worse, believe me." "I could skip the dinners with daddy." Dear old daddy insisted that I call him George. 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. Once we were inside with the door locked, I began to relax a bit. 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. I was stuck. She also had a closet full of clothes, so she wouldn't exactly miss the ones she gave me. What's the problem? You just have to dress as a woman for a week. When she did, George grabbed me and began to kiss me. I needed a place to stay. Couldn't really contribute much to the rent, nor could I save anything toward my own place. "Please don't tell George or Brian." We finished our meal and went back to Carrie's apartment. He got a taxi and took us to one of the nicer places in town. A little later, the guy walked by our table, stopped and put a business card on the table beside me. "I need to change back to my normal clothes now." "That's nice." "I told him to keep his hands off you. We finished eating and George paid the bill, then Brian turned to George. "Our medical plan does not begin until you've completed three months probation. This company is very accepting of LGBT employees, including transgender." She handed me a razor with shaving cream and some hair removal cream. That should have been a warning, but I was so upset about being thrown out, that I missed it. "No, it isn't. In one of my temp jobs, I made friends with Carrie, who had gone to the same college as me. I can't... 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. "Now he knows my name. George again walked out with an arm each around Carrie and I, but with me, I felt his hand slipping down over my ass. We had what amounted to a final interview, which again seemed to go very well. 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. "I promise I will."


"You want a place to live, you're like this for a week, both at the flat, and in public." Carrie took my hand and led me into her bedroom and into her bathroom. "No. We don't want any trouble whatsoever." ... "I can't have a guy here when daddy arrives." "Nail polish, silly, on your fingernails and toenails." "I'm not sure I can pull this off." "No. First, you are a very lucky woman. Hell, rent in the city is damned expensive, and I was living in something not much up from a slum. 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." "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 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. We have a small clinic in house, usually staffed by a nurse practitioner. Let's go get some dinner." "I'll do that sir. George filled us all in. "Carrie, please, I have no place to go." "Yes, ma'am." "I can't fucking win, can I?" I waited about ten minutes before an assistant vice president came in to interview me. Right at 9 o'clock, Brian came out and warmly greeted me. Carrie handed me a cute top, which I put on and a pair of low heels, which did just barely fit. It was a place where I'd never worked before, so they didn't know me. Brian was a friend of George. It blew my mind that having a guy kiss me like that would make me hard, but it was happening. Then she sat me down and did makeup, with base, highlights, eye shadow, and lip stick, among other things. I was glad my panties were holding my cock in check, because I was getting a hard-on. Not if he realizes you aren't paying any rent." "Shit. Then it occurred to me, George and Brian both thought I was a woman. Trust me, you don't want to offend him. Besides I really needed the money. I've got your boy clothes stashed away where my father won't find them." "What are we supposed to do?" "You can't be here. Daddy ordered a bottle of nice wine and poured us each some. I was looking over my shoulder all the way, worried that he might be trying to find out where I live. Get that pretty little ass to bed. I'm not doing your hair every day."


They entered my time worked at the end of the day, and I headed back to the apartment. I've got your boy clothes stashed away where my father won't find them." We sort of limped along like that for a couple of months, until Carrie came home from work one evening, very upset. "You mean...?" "What can we do?" "No. Carrie handed me a cute top, which I put on and a pair of low heels, which did just barely fit. I'll get you some clothes." "Leigh, dear, let's go to the ladies room." "I've got lots of clothes, and you're about my size." The next morning, Carrie took a few minutes to touch up my hair and makeup, before leaving for work. All the same again, plus all the usual. You have to go." "You need to shave off all your body hair -- underarms, back, chest, everything. She was living in a two bedroom place that her father was underwriting for her. Couldn't really contribute much to the rent, nor could I save anything toward my own place. "Even though you have a couple of important people backing you, we still expect you to work hard." "You need to shave off all your body hair -- underarms, back, chest, everything. Now it all seemed to hinge on me continuing to appear to be a woman. We peed, washed our hands and touched up our makeup. He looked like he was still in decent shape and wore an expensive suit. "I totally forgot to do your nails." "Nail polish, silly, on your fingernails and toenails." "No excuses. I didn't care for that, but what could I do without blowing up everything. "What do you mean?" We sort of limped along like that for a couple of months, until Carrie came home from work one evening, very upset. "Even though you have a couple of important people backing you, we still expect you to work hard." "Isn't there anything else we can do?" Carrie looked sympathetic, but adamant. Give me a call." "I can't have a guy living with me, but I could have another woman living with me."


"I am so fucked." "I could skip the dinners with daddy." Carrie used a blow dryer on my hair, styling it with a brush. Hell, rent in the city is damned expensive, and I was living in something not much up from a slum. 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. "Now he knows my name. I needed a place to stay. I figured I'd just hide out inside all day, when I got a call with a temp slot for the day. "So this is your roommate Leigh. 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. I expect you to work your ass off and begin to pay half the rent at that apartment." It's crazy how it all started. Before our meals arrived, Carrie turned to me. "So I'm stuck this way for a week?" "I don't have any women's clothes -- and no money to buy any." "Got rid of him, didn't it?" "Now he knows my name. I was shocked when I looked in the mirror at how much like a girl I looked. Beyond that, George is a very good client of this company, and he recommends you." "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 dressed as nicely as I could -- not sexy, but very business-like. 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. In one of my temp jobs, I made friends with Carrie, who had gone to the same college as me. She had me put on bra and panties, along with a skirt. When I got out of the shower, my guy clothes were gone. "You need to find another place to live for a while." "I know you were probably in the women's restroom at that office today, but be cool." With that, Brian turned to me, and handed me a business card. I expect you to be sober and making a good showing of yourself at your interview tomorrow." "So I'm stuck this way for a week?" She handed me a razor with shaving cream and some hair removal cream. He seemed to think you were just playing hard to get." Carrie gave me several pairs of shoes. 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.


"I told him to keep his hands off you. I looked up one time and saw a guy looking directly at me. As we walked into the restaurant, George had one arm around Carrie's waist, and the other arm around my waist. As we went back Carrie spoke. "I have no intention of letting anyone know I'm not female." I had no idea what he meant or what was going on. Get cleaned up. I'm offering you a way to stay here and avoid having to live on the street." "So what now?" The next morning, Carrie took a few minutes to touch up my hair and makeup, before leaving for work. Please. I went in the women's room, went into a stall, latched the door and sat on the toilet. "Be at our offices at 9 sharp tomorrow morning. We sat and ate our Chinese food, and most of the time no one seemed to pay any attention to us. That's for starters. Why is that a big deal?" Carrie looked sympathetic, but adamant. 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. "You don't understand." "Yes, I know you were assigned male at birth." "You mean...?" "You'd rather live on the street? Okay, take your stuff and get out." "I promise I will." I made sure my appearance was decent, then took the subway to my assignment. He got a taxi and took us to one of the nicer places in town. I went in the women's room, went into a stall, latched the door and sat on the toilet. I wavered between reverie and shock, as George spoke. "So this is your roommate Leigh. We can't... Carrie was about my height and weight, with a cute face, b-cup boobs, and a nice ass. "Tomorrow evening, and he's staying in town for a week. Everyone who interviewed you felt you were qualified for the position. He ushered me back in to an office where there was a vice president waiting to interview me. "That's nice." "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." "I swear, I didn't encourage him." Carrie threw her arms around me and hugged me. Now he thinks I might call him." 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. "I don't know how I'm going to get through this." "I'm not insisting you call him, or that you go out with him. That should have been a warning, but I was so upset about being thrown out, that I missed it. "Well, Leigh, you've done very well. We have made provision though. Now it all seemed to hinge on me continuing to appear to be a woman. "It's long enough, but we need to trim and style it." George took us back to the apartment and walked us up there. All the same again, plus all the usual. 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. "No. This whole thing will fall apart if you don't." "Are you crazy? There's no way in hell I'm calling him back or going out with him." "Are you crazy? There's no way in hell I'm calling him back or going out with him." We peed, washed our hands and touched up our makeup. All the same again, plus all the usual. He looked like he was still in decent shape and wore an expensive suit. "Like I need that shit." "I've looked. We don't want any trouble whatsoever." We went to the Chinese place and Carrie paid. When I got out of the shower, my guy clothes were gone. The man smiled and left. 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. I didn't care for that, but what could I do without blowing up everything. I might be able to pay my way for a change. She had me put on bra and panties, along with a skirt. We don't want any trouble whatsoever." Brian and I talked finance throughout dinner as George and Carrie talked about other things. 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. "I don't know how I'm going to get through this." "I need to cover a few other things before we make an offer. The temp jobs kept coming -- not paying enough for me to get my own place, but I could cover half the food and utilities. You have to go." With that, he turned me around and patted my ass as he gently moved me toward my bedroom. "This is only for a week. "Be at our offices at 9 sharp tomorrow morning. For both our sakes, you need to do this right."


"No excuses. We sat and ate our Chinese food, and most of the time no one seemed to pay any attention to us. She padded out my bra to make it look like I had boobs. I was stuck. Carrie seemed to take great pleasure in all this and looked up at him. Carrie took my hand and led me into her bedroom and into her bathroom. "Sleep well, darling." "Shit." "What can we do?" "Why?" "Just make sure you get that job today. As it turned out, maybe I did. I blushed, which Carrie saw, and figured out why. "Well, I hope to hear from you soon, Leigh." 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. "Okay, Leigh, there's an inexpensive Chinese place down the block. I was surprised how quickly I was catching on to doing my makeup. Get that pretty little ass to bed. I went to the company and got there a little before 9am. 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. 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. Once we were inside with the door locked, I began to relax a bit. "Hell, no." 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. Everyone who interviewed you felt you were qualified for the position. I felt weird as shit, but I guessed it was better than living on the streets and sleeping under bridges. Everyone who interviewed you felt you were qualified for the position. I was looking over my shoulder all the way, worried that he might be trying to find out where I live. As it turned out, maybe I did. Absolutely not." "Since you're being hired as a woman, you'll be expected to dress as a woman and use women's facilities." "That would offend him. I was Leigh, a recent college graduate come to the big city to try to make a success of myself. I've talked to people. He seemed to think you were just playing hard to get." "These are your normal clothes, until daddy is gone. The next morning, Carrie took a few minutes to touch up my hair and makeup, before leaving for work. If Brian found out I wasn't really a woman, George would find out and really be upset. After


what had happened, I damned sure needed alcohol. "Yes, you need to be a very proper young woman." Daddy really wanted Carrie to get a roommate -- female, of course -- to share the rent and relieve him from some of the expense. Carrie seemed to take great pleasure in all this and looked up at him. "My father is coming to town to see how I'm doing." "Trust me, that's the last thing I want." George held me tight for what seemed like an eternity, then gave me a quick kiss, and loosened his hold on me. "Please don't tell George or Brian." "You'd rather live on the street? Okay, take your stuff and get out." "Got rid of him, didn't it?" "This is only for a week. 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." "You know, I think you were right about this young lady. Daddy was late forties or early fifties, with a full head of hair, graying at the temples. If any of this bothers you, please skip this story. Carrie threw her arms around me and hugged me. I expect you to be sober and making a good showing of yourself at your interview tomorrow." "And what if you get some temp assignments while he's here?" Once it was dry and styled, she took scissors and trimmed a bit to make it look more feminine. He has some business in town and he's checking on me while I'm here." With that, Brian turned to me, and handed me a business card. This company is very accepting of LGBT employees, including transgender." "We'll move these clothes to your room, and hide all your boy clothes." 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. Get that pretty little ass to bed. 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. She just might do." We went to the Chinese place and Carrie paid. That should have been a warning, but I was so upset about being thrown out, that I missed it. "Oh God, no." 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. How does one manage to be both ecstatic and depressed at the same


time? Well, I was finding out. Absolutely not." "You mean...?" "When does he get here?" "No. He seemed pretty knowledgeable about finance, and spent some time as we ate delving into how much I knew. She handed me a razor with shaving cream and some hair removal cream. First, you are a very lucky woman. I guessed it wasn't a problem, since it looked like she had more than fifty pairs in her closet. I'm happy to be able to spend time with my daughter and her lovely roommate." They entered my time worked at the end of the day, and I headed back to the apartment. It looks like you have an admirer." "I saw my father pawing you last night after we got back." "Carrie told me you had been looking unsuccessfully for work for a while, only managing temp jobs. I was drunk and my reaction time was seriously impaired, but after a bit of the kissing I pulled back. "Sure thing. You have an opportunity -- take it." "No. That was just a way to make him go away happy." "What can we do?" "You want a place to live, you're like this for a week, both at the flat, and in public." Carrie looked sympathetic, but adamant. 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'm not sure I can pull this off." "This is only for a week. I texted Carrie that I was going to work. "I need to change back to my normal clothes now." I waited about ten minutes before an assistant vice president came in to interview me. I both feared and craved George's touch, and rolled into a fetal position and cried myself to sleep. "Why?" Carrie painted my nails, and we watched cable while they dried. George filled us all in. "It could be a lot worse, believe me." "Yes, I know you were assigned male at birth." "And what if you get some temp assignments while he's here?"


I sat there, totally stunned. She just might do." Carrie painted my nails, and we watched cable while they dried. I looked up one time and saw a guy looking directly at me. Then she gave me a pink nightie, luckily not too sheer and told me to change into that. We have a small clinic in house, usually staffed by a nurse practitioner. And if I got hired, I'd be hired as a woman. I was short and slender for a guy, only about 5'6" and 125 pounds. 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. The man smiled and left. This whole thing will fall apart if you don't." ***** "Better than you'd get through living on the streets." I damned near walked into the men's restroom at one point before I caught myself. It looks like you have an admirer." "Daddy wants to take us to dinner. I guessed it wasn't a problem, since it looked like she had more than fifty pairs in her closet. As my cash was hitting zero and I was about to be thrown out, I ran into Carrie again. Why is that a big deal?" "I have no intention of letting anyone know I'm not female." "Tomorrow evening, and he's staying in town for a week. We have made provision though. Take a minute to freshen up, and we'll go." "Since you're being hired as a woman, you'll be expected to dress as a woman and use women's facilities." ***** George held me tight for what seemed like an eternity, then gave me a quick kiss, and loosened his hold on me. "Leigh is a little shy, but I'll see what I can do with her." "Since you're being hired as a woman, you'll be expected to dress as a woman and use women's facilities." "I'll do that sir. And it looked like I'd be finding out for the indefinite future. I made sure my appearance was decent, then took the subway to my assignment. Don't." "Leigh, dear, let's go to the ladies room." "I saw my father pawing you last night after we got back." "I'll do that sir. 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.


"I have no intention of letting anyone know I'm not female." I thought I'd be dressing as a woman for a week to keep George from throwing me and possibly Carrie out. I was Leigh, a recent college graduate come to the big city to try to make a success of myself. But you need to understand, there will be no interoffice romances or affairs." "Sleep well, darling." "My nails?" "I don't have any women's clothes -- and no money to buy any." 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. 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. 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." "I know you were probably in the women's restroom at that office today, but be cool." "Tomorrow evening, and he's staying in town for a week. I asked for some water, and a woman brought it to me shortly after. "Shit." Carrie took my hand and led me into her bedroom and into her bathroom. "While we are a tolerant company, there are men here who aren't so tolerant in their personal lives. As my cash was hitting zero and I was about to be thrown out, I ran into Carrie again. We can't... She had no intention of making me her lover. If any of this bothers you, please skip this story. "I want a job, I just wasn't looking to be employed as a woman." "How does that help?" "Just make sure you get that job today. Get cleaned up. As we went back Carrie spoke. 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. Then she paused, looked thoughtful, then looked me over carefully. And again told me I needed to learn to do my own. "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. That was just a way to make him go away happy." "Now we need to do something about your hair." "That is strictly between you and me. I'm happy to be able to spend time with my daughter and her lovely roommate." I sat there, totally stunned. I drained my glass of wine, and another one shortly after. For both our sakes, you need to do this right."


"I can't fucking win, can I?" "When does he get here?" "Trust me, that's the last thing I want." "I've looked. Just let me change and clean off this makeup." ... George offered a toast to me assuming I'd be hired the next day. And again told me I needed to learn to do my own. We peed, washed our hands and touched up our makeup. We finished eating and George paid the bill, then Brian turned to George. "Just make sure you get that job today. George again walked out with an arm each around Carrie and I, but with me, I felt his hand slipping down over my ass. Let's go get some dinner." Carrie gave me several pairs of shoes. I shaved my face again, along with my armpits, then my legs, and put the hair remover on my chest and arms. As we walked into the restaurant, George had one arm around Carrie's waist, and the other arm around my waist. I expect you to work your ass off and begin to pay half the rent at that apartment." "Please don't tell George or Brian." Report Story byjackie_emŠ 7 comments/ 25033 views/ 24 favorites Report Story Report Story "When does he get here?" I sat there, totally stunned. Now, at last it looked like I'd have a job, but only by continuing to dress and act like a woman. 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. . After months of scraping by, I might now have a chance to really get a half decent full time job. We have a small clinic in house, usually staffed by a nurse practitioner. She had zero interest in a romantic relationship, not that I could afford to take her out anyhow. "What are we supposed to do?" With that, Brian turned to me, and handed me a business card. My mind was so blown at that point, I'd gone numb. When our eyes met, he gave me the biggest smile. We returned to the table, and there was another man there with George. He has some business in town and he's checking on me while I'm here."


"Oh God, no." "Yes, you need to be a very proper young woman." "That would offend him. George introduced him as Brian. First, you are a very lucky woman. She told me I could stay there for a little while, as I tried to get on my feet. 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. I damned near walked into the men's restroom at one point before I caught myself. Then again, I figured she could have them back in a week, after daddy left. "I'm not insisting you call him, or that you go out with him. I found that Brian was a senior VP and the boss of the first VP who had interviewed me. Let's go get some dinner." "What do you mean?" "Shit." The first part of the evening, Carrie brought daddy up to date on what was going on. I can't afford my own place and I can't find anyone else who'll take me in." "And what if you get some temp assignments while he's here?" Brian and I talked finance throughout dinner as George and Carrie talked about other things. It blew my mind that having a guy kiss me like that would make me hard, but it was happening. "You seem to be a nice girl, and I know you haven't been able to carry your share. Can't you do my hair and makeup for a week?" With that, he turned me around and patted my ass as he gently moved me toward my bedroom. "So what now?" "Our medical plan does not begin until you've completed three months probation. She had me put on bra and panties, along with a skirt. Brian seemed interested in my college background and my degree in finance. I gave it a few minutes, then showered it off. The temp jobs kept coming -- not paying enough for me to get my own place, but I could cover half the food and utilities. After months of scraping by, I might now have a chance to really get a half decent full time job. George again walked out with an arm each around Carrie and I, but with me, I felt his hand slipping down over my ass. I can't... That can be used for any medical problems until the insurance kicks in." "You need to find another place to live for a while." "Follow me." George offered a toast to me assuming I'd be hired the next day. I blushed, which Carrie saw, and figured out why. "Oh God, no."


"No chance of that." I was struggling to pay rent with only stray temp jobs, when I hit a dry spell. I gave it a few minutes, then showered it off. I've got razors and depilatory cream. I texted Carrie that I was going to work. "Daddy wants to take us to dinner. Separate bedrooms and separate beds only. When she did, George grabbed me and began to kiss me. I found that Brian was a senior VP and the boss of the first VP who had interviewed me. Give me a call." "No. That's for starters. Before our meals arrived, Carrie turned to me. "You're right, I don't. That was just a way to make him go away happy." "Are you crazy? There's no way in hell I'm calling him back or going out with him." "You need to find another place to live for a while." "No chance of that." "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. Separate bedrooms and separate beds only. That's for starters. If I screwed up, George would know and my ass would be on the street. After lunch, he took me to Human Resources where I met Katherine, who was manager of that function. I had no idea what he meant or what was going on. The temp jobs kept coming -- not paying enough for me to get my own place, but I could cover half the food and utilities. I'll get you some clothes." "Well, Leigh honey. But you need to understand, there will be no interoffice romances or affairs." George took us back to the apartment and walked us up there. Beyond that, George is a very good client of this company, and he recommends you." "No. You're coming like that." "Jeez, do you have to?" "I promise I will." I dressed as nicely as I could -- not sexy, but very business-like. I asked for some water, and a woman brought it to me shortly after. "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." "I can't have a guy living with me, but I could have another woman living with me." We went to the Chinese place and Carrie paid. We returned to the table, and there was another man there with George. As it turned out, maybe I did. I drained my glass of wine, and another one shortly after. He seemed to think you were just playing hard to get." With that, he turned me around and patted my ass as he gently moved me toward my bedroom.


"You seem to be a nice girl, and I know you haven't been able to carry your share. 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. She padded out my bra to make it look like I had boobs. "I don't know how I'm going to get through this." "I don't have any women's clothes -- and no money to buy any." "Leigh, dear, let's go to the ladies room." "You mean I'm hired?" "Well, Leigh, you've done very well. 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. Hell, rent in the city is damned expensive, and I was living in something not much up from a slum. I moved in Carrie's extra bedroom, assuming I'd get a job and be able to move out. They would expect me to show up and interview as a woman. I'm offering you a way to stay here and avoid having to live on the street." "Carrie, please, I have no place to go." "Well, Leigh honey. I'm happy to be able to spend time with my daughter and her lovely roommate." "You should be so lucky." 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 was Leigh, a recent college graduate come to the big city to try to make a success of myself. I drained my glass of wine, and another one shortly after. Don't." "I know you were probably in the women's restroom at that office today, but be cool." "You need to shave off all your body hair -- underarms, back, chest, everything. We returned to the table, and there was another man there with George. That can be used for any medical problems until the insurance kicks in." "I need to cover a few other things before we make an offer. Trust me, you don't want to offend him. She told me I could stay there for a little while, as I tried to get on my feet. 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. "While we are a tolerant company, there are men here who aren't so tolerant in their personal lives. I told the receptionist that I was there for a job interview, and she had me take a seat in the lobby. He looked like he was still in decent shape and wore an expensive suit. "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 want a job, I just wasn't looking to be employed as a woman." "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. You have an opportunity -- take it."


"I swear, I didn't encourage him." "I'm not insisting you call him, or that you go out with him. Then she sat me down and did makeup, with base, highlights, eye shadow, and lip stick, among other things. We finished eating and George paid the bill, then Brian turned to George. "Hell, no." "So what now?" I made sure my appearance was decent, then took the subway to my assignment. She had no intention of making me her lover. We have made provision though. They would expect me to show up and interview as a woman. "I totally forgot to do your nails." George stopped kissing me but still held me tightly against him. I guessed it wasn't a problem, since it looked like she had more than fifty pairs in her closet. I figured I'd just hide out inside all day, when I got a call with a temp slot for the day. Then it occurred to me, George and Brian both thought I was a woman. She had zero interest in a romantic relationship, not that I could afford to take her out anyhow. "Yes, ma'am." "Fuck." "Basically, no. Brian seemed interested in my college background and my degree in finance. Just let me change and clean off this makeup." "Carrie told me you had been looking unsuccessfully for work for a while, only managing temp jobs. We can't... I really appreciate the opportunity." "Jeez, do you have to?" "Our medical plan does not begin until you've completed three months probation. She was living in a two bedroom place that her father was underwriting for her. He came in with us, and Carrie immediately hit the bathroom. It looks like you have an admirer." "That would offend him. I shaved my face again, along with my armpits, then my legs, and put the hair remover on my chest and arms. Now, at last it looked like I'd have a job, but only by continuing to dress and act like a woman. 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." I avoided looking in the direction of that guy, though it was hard to ignore his apparent interest. Now he thinks I might call him." Carrie painted my nails, and we watched cable while they dried. And if I got hired, I'd be hired as a woman. Brian and I talked finance throughout dinner as George and Carrie talked about other things. 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. He came in with us, and Carrie immediately hit the bathroom. She was living in a two bedroom place that her father was underwriting for her. I expect you to be sober and making a good showing of yourself at your interview tomorrow." "No. Brian was a friend of George. All the wine started to go to my head, and when we left, I was almost staggering. I didn't care for that, but what could I do without blowing up everything. How does one manage to be both ecstatic and depressed at the same time? Well, I was finding out. This contains cross dressing, non-consensual sex, gender bending/change, and sex between the protagonist and both a male and a female. She had me take off my shirt and slathered it on my back, not that I had a lot of hair there anyhow. After what had happened, I damned sure needed alcohol. ... They entered my time worked at the end of the day, and I headed back to the apartment. If I screwed up, George would know and my ass would be on the street. They would expect me to show up and interview as a woman. After lunch, he took me to Human Resources where I met Katherine, who was manager of that function. Daddy really wanted Carrie to get a roommate -- female, of course -- to share the rent and relieve him from some of the expense. As we walked into the restaurant, George had one arm around Carrie's waist, and the other arm around my waist. I was surprised how quickly I was catching on to doing my makeup. Then she gave me a pink nightie, luckily not too sheer and told me to change into that. She padded out my bra to make it look like I had boobs. 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. This contains cross dressing, non-consensual sex, gender bending/change, and sex between the protagonist and both a male and a female. I moved in Carrie's extra bedroom, assuming I'd get a job and be able to move out. I figured I'd just hide out inside all day, when I got a call with a temp slot for the day. Why is that a big deal?" "All right, then. After lunch, he took me to Human Resources where I met Katherine, who was manager of that function. "My nails?" "Pay attention to what I'm doing. If any of this bothers you, please skip this story. "I totally forgot to do your nails." "You should be so lucky." At that point, I'd have about sold my soul to avoid living on the streets. I was short and slender for a guy, only about 5'6" and 125 pounds. As we went back Carrie spoke. "You know, I think you were right about this young lady. I really appreciate the opportunity." George took us back to the apartment and walked us up there. Daddy was late forties or early fifties, with a full head of hair, graying at the temples. 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. I was glad my panties were tranny webcams holding my cock in check, because I was getting a hard-on. Besides I really needed the money. As my cash was hitting zero and I was about to be thrown out, I ran into Carrie again. When our eyes met, he gave me the biggest smile. What do we need to do?" "Carrie told me you had been looking unsuccessfully for work for a while, only managing temp jobs. Now it all seemed to hinge on me continuing to appear to be a woman. 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. That was a blessing, and they just seemed to accept that their temp was a woman named Leigh. I gave it a few minutes, then showered it off. Just let me change and clean off this makeup." "These are your normal clothes, until daddy is gone. This company is very accepting of LGBT employees, including transgender." "I can't fucking win, can I?" "How does that help?" "Well, Leigh honey. Carrie was about my height and weight, with a cute face, b-cup boobs, and a nice ass. George held me tight for what seemed like an eternity, then gave me a quick kiss, and loosened his hold on me. At that point, I'd have about sold my soul to avoid living on the streets. We sat and ate our Chinese food, and most of the time no one seemed to pay any attention to us. Carrie handed me a cute top, which I put on and a pair of low heels, which did just barely fit. Take a minute to freshen up, and we'll go." "Fuck." "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. "While we are a tolerant company, there are men here who aren't so tolerant in their personal lives. George introduced him as Brian. If Brian found out I wasn't really a woman, George would find out and really be upset. I asked for some water, and a woman brought it to me shortly after. I damned near walked into the men's restroom at one point before I caught myself. Please. George introduced him as Brian. She had no intention of making me her lover. That was a blessing, and they just seemed to accept that their temp was a woman named Leigh. I'm not doing your hair every day." "I am so fucked." "Hell, no." "Yes, ma'am." "I'm not sure I can pull this off."


"My father is coming to town to see how I'm doing." Daddy really wanted Carrie to get a roommate -- female, of course -- to share the rent and relieve him from some of the expense. Then it occurred to me, George and Brian both thought I was a woman. Not if he realizes you aren't paying any rent." "Daddy wants to take us to dinner. 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. George offered a toast to me assuming I'd be hired the next day. Can't you do my hair and makeup for a week?" "You mean I'm hired?" Carrie used a blow dryer on my hair, styling it with a brush. I was looking over my shoulder all the way, worried that he might be trying to find out where I live. So nice to meet you, darling. Daddy was late forties or early fifties, with a full head of hair, graying at the temples. She had zero interest in a romantic relationship, not that I could afford to take her out anyhow. "Pay attention to what I'm doing. I went in the women's room, went into a stall, latched the door and sat on the toilet. "Now we need to do something about your hair." "There's no way I'm going to a temp assignment looking like this." "No, it isn't. What do we need to do?" We sort of limped along like that for a couple of months, until Carrie came home from work one evening, very upset. "Even though you have a couple of important people backing you, we still expect you to work hard." "Well, Leigh, you've done very well. Then she sat me down and did makeup, with base, highlights, eye shadow, and lip stick, among other things. Not if he realizes you aren't paying any rent." "You don't understand." "No, it isn't. 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 texted Carrie that I was going to work. "All right, then. "I can't have a guy living with me, but I could have another woman living with me." "I've got lots of clothes, and you're about my size." ... "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. 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. She just might do."


"Follow me." "Fuck." I dressed as nicely as I could -- not sexy, but very business-like. I felt weird as shit, but I guessed it was better than living on the streets and sleeping under bridges. That was a blessing, and they just seemed to accept that their temp was a woman named Leigh. Brian seemed interested in my college background and my degree in finance. I needed the job. You're coming like that." "My father is coming to town to see how I'm doing." ... This contains cross dressing, non-consensual sex, gender bending/change, and sex between the protagonist and both a male and a female. It blew my mind that having a guy kiss me like that would make me hard, but it was happening. He ushered me back in to an office where there was a vice president waiting to interview me. "My nails?" "Okay, Leigh, there's an inexpensive Chinese place down the block. That can be used for any medical problems until the insurance kicks in." "You should be so lucky." 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. Couldn't really contribute much to the rent, nor could I save anything toward my own place. I waited about ten minutes before an assistant vice president came in 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. All the wine started to go to my head, and when we left, I was almost staggering. After months of scraping by, I might now have a chance to really get a half decent full time job. I have a job, and don't have time to do my own makeup and hair and yours too." "That is strictly between you and me. And again told me I needed to learn to do my own. "Pay attention to what I'm doing. He seemed pretty knowledgeable about finance, and spent some time as we ate delving into how much I knew. "Sure thing. She also had a closet full of clothes, so she wouldn't exactly miss the ones she gave me. My mind was so blown at that point, I'd gone numb. When our eyes met, he gave me the biggest smile. A little later, the guy walked by our table, stopped and put a business card on the table beside me. I thought I'd be dressing as a woman for a week to keep George from throwing me and possibly Carrie out. I felt weird as shit, but I guessed it was better than living on the streets and sleeping under bridges. I can't... Besides I really needed the money. 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.


What's the problem? You just have to dress as a woman for a week. And it looked like I'd be finding out for the indefinite future. "You can't be here. And it looked like I'd be finding out for the indefinite future. We finished our meal and went back to Carrie's apartment. Then she paused, looked thoughtful, then looked me over carefully. It was a place where I'd never worked before, so they didn't know me. Separate bedrooms and separate beds only. I have a job, and don't have time to do my own makeup and hair and yours too." "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." "So this is your roommate Leigh. I was surprised how quickly I was catching on to doing my makeup. What's the problem? You just have to dress as a woman for a week. I have a job, and don't have time to do my own makeup and hair and yours too." "These are your normal clothes, until daddy is gone. My mind was so blown at that point, I'd gone numb. But you need to understand, there will be no interoffice romances or affairs." "We'll move these clothes to your room, and hide all your boy clothes." "You want a place to live, you're like this for a week, both at the flat, and in public." "I need to change back to my normal clothes now." "No. If Brian found out I wasn't really a woman, George would find out and really be upset. Trust me, you don't want to offend him. I'll get you some clothes." "Sleep well, darling." At that point, I'd have about sold my soul to avoid living on the streets. Once we were inside with the door locked, I began to relax a bit. "I've looked. When I got out of the shower, my guy clothes were gone. "Okay, Leigh, there's an inexpensive Chinese place down the block. Please. I went to the company and got there a little before 9am. Now he thinks I might call him." "Nail polish, silly, on your fingernails and toenails." We finished our meal and went back to Carrie's apartment. Then again, I figured she could have them back in a week, after daddy left. "You know, I think you were right about this young lady. She also had a closet full of clothes, so she wouldn't exactly miss the ones she gave me. Take a minute to freshen up, and we'll go." "Jeez, do you have to?" Once it was dry and styled, she took scissors and trimmed a bit to make it look more feminine. I told the receptionist that I was there for a job interview, and she had me take a seat in the lobby. So nice


to meet you, darling. 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. Before our meals arrived, Carrie turned to me. "I told him to keep his hands off you. If I screwed up, George would know and my ass would be on the street. Daddy ordered a bottle of nice wine and poured us each some. I can't afford my own place and I can't find anyone else who'll take me in." "What do you mean?" "We'll move these clothes to your room, and hide all your boy clothes." I had no idea what he meant or what was going on. I was short and slender for a guy, only about 5'6" and 125 pounds. Dear old daddy insisted that I call him George. Brian was a friend of George. Daddy won't like the fact that a guy is living here with me -- a guy who isn't even paying half the rent." "Daddy will probably take us out to dinner a few times while he's here, so you might as well get used to it." George stopped kissing me but still held me tightly against him. I moved in Carrie's extra bedroom, assuming I'd get a job and be able to move out. Then she paused, looked thoughtful, then looked me over carefully. She told me I could stay there for a little while, as I tried to get on my feet. You're coming like that." "All right, then. I thought about him every time I was about to look in that direction, and I think I blushed a couple more times. In one of my temp jobs, I made friends with Carrie, who had gone to the same college as me. I wavered between reverie and shock, as George spoke. "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." "I can't have a guy here when daddy arrives." "Shit. I shaved my face again, along with my armpits, then my legs, and put the hair remover on my chest and arms. I was glad my panties were holding my cock in check, because I was getting a hardon. He got a taxi and took us to one of the nicer places in town. I needed the job. You have an opportunity -- take it." "No. If any of this bothers you, please skip this story. 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. Then she gave me a pink nightie, luckily not too sheer and told me to change into that. 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." 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. Once it was dry and styled, she took scissors and trimmed a bit to make it look more feminine. After


what had happened, I damned sure needed alcohol. "How does that help?" I was struggling to pay rent with only stray temp jobs, when I hit a dry spell. This whole thing will fall apart if you don't." "Why?" "Like I need that shit." "I saw my father pawing you last night after we got back." I was stuck. And if I got hired, I'd be hired as a woman. I both feared and craved George's touch, and rolled into a fetal position and cried myself to sleep. "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. "Basically, no. Right at 9 o'clock, Brian came out and warmly greeted me. George filled us all in.

"There's no way I'm going to a temp assignment looking like this." "That's nice." "Trust me, that's the last thing I want." "Isn't there anything else we can do?" "Like I need that shit." "You mean I'm hired?" It's crazy how it all started. I'm offering you a way to stay here and avoid having to live on the street." "No excuses. Daddy ordered a bottle of nice wine and poured us each some. Carrie seemed to take great pleasure in all this and looked up at him. This contains cross dressing, non-consensual sex, gender bending/change, and sex between the protagonist and both a male and a female. "Better than you'd get through living on the streets." "I need to cover a few other things before we make an offer. What do we need to do?" "Sure thing. I looked up one time and saw a guy looking directly at me

The Roommate Transsexuals & Crossdressers  

I found that Brian was a senior VP and the boss of the first VP who had interviewed me. She had me take off my shirt and slathered it on my...

The Roommate Transsexuals & Crossdressers  

I found that Brian was a senior VP and the boss of the first VP who had interviewed me. She had me take off my shirt and slathered it on my...

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