The Roommate

"I'm generally pretty healthy, but that's nice to know."

"Are you currently on hormone replacement therapy?"

"No. Why?"

"Why aren't you?"

"I... I haven't been able to afford it."

"I'll take you to the clinic right now. They can start you on HRT. She can give you shots, until insurance covers it."

"Do I appreciate it, but it isn't really necessary."

"It's just part of the benefits. Besides, you'll be working here as a woman, and HRT will ease your transition."

"I don't want to be a burden."

"It's no burden, it's just a side benefit of employment."

I couldn't think of a way to politely decline hormone replacement, without raising suspicions. Katherine escorted me to the clinic, where I got a shot. The nurse practitioner told me it would inhibit body hair and promote secondary female body characteristics. I didn't really like that, but short of blowing up the job and ending up on the streets, I guessed I'd be doing HRT.

Katherine gave me an official job offer at a very respectable salary for someone with a degree but no experience. It was Friday, and I was to start on Monday morning. I called Carrie to tell her I had the job, and she was delighted for me. I wrapped up everything at the company and headed back to the apartment.

On the subway ride home, I had a guy try to chat me up and ask me out on a date. I lied and told him I had a boyfriend who would not approve. I kept wondering how the hell I am going to cope, not just with pretending to be a woman for a week, but honestly until I can make and save enough money to ditch that job and find a job and flat where I can be a guy.

George was at the apartment when I got there. Carrie was in her room getting ready, since George wanted to take us out to celebrate my new job. I scurried to my room as quickly as I could, but could not manage to do that before George gave me a big hug in which one hand snuck down over my ass again. At least this time he didn't try to kiss me. I still had a hard-on as I went on my room.

Why is it that a guy grabbing my ass seems to turn me on? I can't figure it out. Is dressing like this turning me gay? Was I always gay and never admitted it? I don't think so. I still get turned on by looking at women, but not by men. I like to see pix of naked women, and don't care about pix of naked guys. At least I don't think so. Shit. Do I even know myself anymore?

I fixed myself up as best I could in my bedroom. When I heard Carrie come out and talk to George, I quickly ducked into the bathroom to pee and touch up my makeup. Carrie had the bedroom with the attached bath. I had to use the second bath and exit my room to get there. That's a little inconvenient when I want to dodge someone in the living room.

George took us out to another nice dinner. He bought a bottle of wine, but I learned from last night and took it easy on the alcohol. I really needed a drink from all that happened, but had no intention of getting drunk around George. I know Carrie said she told George to back off, but I still don't trust him. Again, he had his arms around the both of us as we entered the restaurant, and again his hand slipped down over my ass.

After dinner, George suggested we celebrate by going to a club. Carrie thought that was a great idea, but I wasn't quite so sure. I did drink some but only very slowly, though Carrie seemed to be drinking like there was no tomorrow. A guy asked Carrie to dance, and she went with him to the dance floor. George then asked me to dance. I tried to politely decline, but with little success.

We went out there during a fast dance, and it wasn't too bad. I could keep my distance and pretend I was dancing with others, rather than with George. After the fast dance, a slow number came on. He quickly grabbed me and pulled me close. George pulled me tight against him and had one hand running up and down my back as the other one was all over my ass. The slow number ended and he gave me a long kiss before I could get away.

I ducked in the women's restroom, went in a stall and just sat and shook for a few minutes. I was repelled by having a guy kiss me and feel me up, but at the same time I was turned on and had a massive hard-on. Once I felt like I was back under control, I peed and touched up my makeup. As I was finishing up, Carrie came in the restroom to check on me.

"You okay, Leigh? Daddy was getting worried about you."

"If I can keep your daddy from kissing me and feeling up my ass, I'll be a lot better."

"I'm sure he doesn't mean anything by it."

"I wish I were as certain of that as you seem to be. How do you think he'd react if he knew I had a prick?"

"It'll never get that far."

"I sure as hell hope not."

"Shit, girl, you'd probably enjoy it if it did."

"Screw you."

"You're sure as hell not doing that."

"Just tell your daddy that my period is starting and I need to go home and rest."

"Shit, and I was just starting to have some fun."

"Why don't you and George stay here and have fun while I go back to the flat?"

I let Carrie go out first, and I followed a minute later. George was sympathetic about my 'condition'.

"Why don't I escort you back to the apartment while Carrie enjoys herself?"

"I'll be fine, but Carrie has had a little too much to drink and you need to make sure she's fine."

"Really, I feel responsible for getting you safely back home."

Yeah, I'll bet you do, I thought. You just want to go back to the apartment and fuck your little girl's roommate. I wasn't nearly drunk enough to give him the chance to try.

"The subways can be so bad at night. You need someone to escort you."

"I'll take an Uber. I'll be fine. I've been living here for almost a year. I've learned a little bit about taking care of myself."

As a guy, that was true. As a woman, I didn't know shit about taking care of myself, but I figured my odds were better with stray people on the street than with George. I insisted on going alone and on having him stay with Carrie. Finally, he agreed, but before I left, he gave me another hug and kiss, feeling up my ass again.

I got back to the apartment safely, went in my bedroom and locked the door. Much later, I heard Carrie and George return, and they both sounded pretty wasted. I couldn't tell much except that they were laughing and giggling and stumbling around the place. Things quieted down and a little later, I heard a gentle tapping on my bedroom door. I figured it was Carrie checking on me.

I got up and opened the door to find George standing there.

"I wanted to make sure you were okay."

"Thank you, George. I'll be fine."

"Could we talk for a minute?"

"What about?"

"May I come in, Leigh?"

I reluctantly opened the door and let George in. My mind was screaming that this was a terrible idea, but I didn't know how to politely avoid it. I was wearing my pink nightie, which as I said was not sheer, for which I was very glad. He sat down on the bed, and patted the bed to indicate he wanted me to sit by him.

I sat down, but father away, only to have him move closer to me on the bed. He put an arm around me and I got very uneasy.

"Look, George -- I really can't..."

"I understand. It's that time of the month, and there are things that are uncomfortable."

"It's not just that -- you're Carrie's father and a married man."

"My marriage has been a shambles for years now. We stay married, but there's no love and no affection. We stay together because divorce would destroy our finances."

"Look, I understand people have bad marriages, but I can't..."

"I need someone to hold, someone to kiss, someone to please me. My wife hasn't done that for a long time."

"And I can't do that now."

"You're a very pretty girl -- very sweet. And I'm glad I was able to help you get a job after your long struggle to find employment. I just thought maybe you'd appreciate my help."

"I do appreciate your help -- very much."

"And thought maybe you could show your appreciation by making me feel good."

"George, I don't think -- "

"Don't think, sweetie, just do it. I know you can't fuck, but there are other things you could do to make me feel good."

"George, please don't."

"Leigh, honey. It won't take long. Just suck me off -- make me cum, and I'll go away happy."

"You don't understand."

"It shouldn't be that big a deal, honey. Girls do that for guys all the time. And I'd feel so much better and know you really did appreciate what I did for you."

"George, I do appreciate it."

"And I subsidize the apartment where you've been living without paying rent."

"George, please don't make me do this."

"I don't want to make you do anything. I just want you to show me how much you appreciate the job, the apartment, the dinners while I've been here."

I'd never sucked a dick in my life. I'd never even touched another guy's junk. I was a lot smaller than George was and I couldn't force him out of my bedroom, and didn't know how to get rid of him without doing something like that. And I was tired and knew George would go as far as he thought he could get away with, if I didn't give him something.

"What if I stroke it for you?"

"Would you do that?"

"One time -- one time only. Tonight -- never again. Nothing more -- no sex -- nothing."

George kissed me, putting his tongue deep into my mouth, then pulled back and unzipped his pants. He pulled out his cock, which honestly was no bigger than mine -- about six inches. He took my hand and put it on his prick. I very delicately touched the top of his dick, then gently stroked the underside. George moaned and lay back on the bed.

I had some hand cream on the night stand, since Carrie insisted I moisturize my skin, and got a dollop of hand cream and used that to lubricate my hand as I stroked him. His cock was hard and George moaned and moved his hips as his dick twitched and a drop of pre-cum formed at the tip.

"Please Leigh, kiss it, take it in your mouth."

George gently pushed my head toward his prick, and I am ashamed to admit, I let him. I just wanted him to cum and get the hell out of there. I was ready to do anything that would get rid of him. I hated it, but took the head of his cock between my lips. I could see red from my lipstick on the end of his dick before I went back for a second pass, taking just a little more of it.

"Please, suck it, make me cum, baby."

I kept stroking his prick with one hand as I gradually worked my way to taking half of it in my mouth. All of a sudden, he grabbed my head and held it tight, as George erupted in my mouth. I swear, the first blast almost knocked off my tonsils, before he filled my mouth with a great gush of his sperm. I struggled to breathe as he held me while pumping what felt like gallons of cum down my throat.

"Swallow it, baby. For me."

I didn't have much choice but to swallow it. It was either that or be drowned in his cum. As it was, it took a couple of swallows to get it all down. George let me go, then brought my face up near his and kissed me on the cheek. Normally, he'd kiss me on the mouth, but I guess he didn't want to taste his own cum on my lips.

"That was great, Leigh baby."

"George, you said if I did that, you'd go and not ask anything more."

"You need your rest, and I guess I should get back to my hotel. Thanks, doll."

George tucked his dick back in his pants, zipped up and staggered to the door. I followed him so I could close and lock it behind him. Before he left, he grabbed me again and groped my ass with one hand as the other one went for a boob. I still had my bra on, and he felt up the bra and padding, since there was no real boob there.

He finally let go of me and left the room. I quickly closed and locked the door. I went back and curled up in a ball on the bed. I wept over having sucked off a guy who groped and kissed me. What had happened to me? What had happened to my life? Was I becoming gay? Was this becoming more than just something I did to have a place to stay? I fell asleep crying.

...

The next day, George wanted to spend with Carrie and me. I begged off, saying I had cramps from my period, my non-existent period, as it were. I begged off on all activities involving George both Saturday and Sunday. I was too ashamed to even tell Carrie what George had coerced me into doing. I consented, and in a way, that made it far worse.

Monday morning, I showered, dressed, did my hair and makeup and went in for my first day of work at the job George helped me get. Part of the day was spent in orientation and filling out all my HR paperwork, but I was assigned a cube and computer and put to some real work before the day was out. It was nothing too complex, some Excel spreadsheets of financial data that I had to crunch.

I mostly avoided George in the evenings, saying I was having a long and especially difficult period. I only told Carrie that I was not comfortable being around George that much.

"Carrie, I am really scared that the more he sees of me, the more likely he is to figure out I'm not really a woman."

"Leigh, he bought it completely."

"Still -- "

On George's last night in town before heading home, he insisted on taking us all out to dinner. I tried unsuccessfully to get out of it. Again, it was a very nice restaurant, and George got another bottle of wine. I tried to avoid drinking, but they'd have none of that, so I drank as little wine as possible and as slowly as possible.

When he brought us back to the apartment, Carrie again disappeared instantly and George followed me into my bedroom before I could stop him. Need I even bother saying what he wanted? He wanted me to suck him off again. I guess I'm lucky he didn't want to fuck me. George was quite happy with a blowjob, so again I gave it to him to get rid of him.

Carrie saw George off the next day, and I was glad to see him go. Because of the job, I still had to dress as a woman, but at least I didn't have George wanting me to suck him off.

Work went well. I did pivot tables and lookup queries in Excel, and consolidated data to pull meaningful numbers out of it. I even did Access queries to pull additional data. I have to say that I enjoyed the work. I love crunching numbers, and I have a decent aptitude for it. At the end of the week, even my new boss seemed pleased at what I'd managed to do.

I was the only woman in the department, assuming you considered me a woman. They all seemed to accept me as one, and most of them were initially a bit contemptuous of a woman in that role, but as they began to see my work, they became more accepting. Everyone kind of took it as gospel that men are better at math and women at language, and they assumed I was a woman.

I had assignments to prepare data for upper management, and build PowerPoint slides for the presentation. Apparently the staff in that department rotated the responsibility of presenting the results to upper management, including Brian. Since I was the newby, they dropped this on me the first go around.

I made damned sure I knew the numbers and what that meant with respect to the business. Honestly, I think some of them wanted me on the firing line because they hoped I'd fail and they'd be rid of me. Instead, I gave a poised, confident, and knowledgeable presentation. Brian and the others were pleased.

"You've only been here a short time, Leigh, but you've really gotten a good grasp of the business in that time. I hired you as a favor to George, but you have a future here if you want it."

Brian took me under his wing and began to really mentor me. I learned a lot more about the company, its management, and its business. He told me a lot about some of the foibles of some of the other top managers and how best to deal with them. I found myself to be considered a rising star in the company, which made a few of my co-workers jealous. Then again, they didn't want to cross me either.

I was walking on air, until I thought about it and realized my future meant continuing to be a woman. The clinic at work continued to give me HRT shots and I began to feel some of the effects. I started to get real boobs, which disturbed the hell out of me. My hips got rounder and my body shape began to change.

I didn't have to worry so much about body hair, as it got thinner, and lighter. I still needed to shave my face, legs, and underarms, but I'd never had a great amount of facial hair anyhow. The longer this lasted, the more like a woman I was beginning to look. Even the appearance, softness, and aroma of my skin changed slightly. My only consolation was that most of the changes would go away once I stopped the HRT.

At home, Carrie became warmer, the longer we went on. We'd often sit together of the sofa watching movies and laughing or crying over what happened in them. One evening, after a very romantic scene in one movie, Carrie turned and kissed me.

"I'm sorry, Leigh. I've always been attracted to women, and I've really begun to see you as one."

"I hate to say this, but I've begun to feel like one."

Carrie brushed my hair away from my face, then kissed me again.

"Is that so bad?"

"When you're kissing me, it's almost tolerable."

"It's strange. I'm both attracted and repelled at the same time. I know you're a guy and that repels me, but you are so sweet and pretty that I'm also attracted."

"I've always been attracted to you, Carrie."

"I don't know how far I'm willing to go, Leigh, but we can find out."

"I'm willing to go as far as you'll let me."

We kissed and I tried not to push it. After having George push me where I didn't want to go, I didn't want to do the same thing to Carrie. We spent a long time just kissing and touching each other before Carrie took my hand and led me into her bedroom. We lay down on her bed and continued to kiss and touch, until she took off her top.

I took that as permission to touch her boobs, at least through her bra, so I began stroking them as we kissed. Carrie began stroking my boobs and to my surprise, I could feel something and it was pleasurable. I had avoided touching my boobs. They just reminded me that I was living as a woman. Even when I showered, I didn't touch them but just let the water rinse them off.

If Carrie wanted to touch my boobs and it felt decent, I decided I ought to let her. She got me into this situation, but that kept me off the streets and got me a job. I took off my top and we both took off our bras. I was only an a-cup, while Carrie had b-cup boobs, but I liked touching her boobs and reluctantly found I enjoyed having her touch mine.

I've always enjoyed touching women's breasts, and enjoyed Carrie's as well. I sweetly but firmly caressed them, then proceeded to kissing and sucking on them, paying lots of attention to her nipples which looked so much like they wanted the attention. They stood way up and Carrie moaned as I played with them. I continued until Carrie came, just from me playing with her boobs.

As Carrie came down off her orgasm, she began to really pay attention to my boobs. I was amazed at how delicious it felt having her kiss and fondle my tits. As I said I had avoided touching them and never realized just how sensitive they were. As she kissed and touched them, I felt a heat rising through my body , the likes of which I'd never felt before.

I moaned and arched my back from the pleasure, without any conscious thought, without even really wanting to. I was more than willing to give her pleasure this way, but the idea of her stimulating me this way still seemed alien. I felt waves of heat and pleasure rolling through my body, quite unlike anything I'd ever felt in sex before, and realized I'd probably just had a female orgasm.

I was a little freaked out at the thought of having female orgasm -- I could tell I hadn't ejaculated. So as a distraction, I returned to trying to pleasure Carrie. I unzipped her skirt, and she lifted her hips for me to slide skirt and panties off. I got a good look at her sweet little pussy. She had a little strip of hair above it, and had shaved the rest.