All To Win Her Over

by Jennifer White

 

I stood there, and I was just stunned. It was like I had been hit with a lightning bolt. I just saw, by far, the best looking woman I had ever seen in my life. Even all the college girls I had, or my senior spring break to Ft. Lauderdale with all the hotties, nothing came close to her. And here she was, working in the same office as I was!

I did a little research on her, and I found out that she was (obviously) the most desirable girl in the whole company, and that every man was after her. But she had a policy of not dating men from the office, so she shot them all down, one at a time. Her name was Tawny, which made me laugh, because who names their daughter Tawny? It sounded more like a stage name for a stripper. But no, that was her real name.

I would take a route to the copier that was out of the way, just to walk by her desk. She even *smelled* good, when I got close enough to her. Of course, she had perfect full lush blonde hair, long legs, a perfect figure, large breasts, and she tended to wear little tight skirts and high heels. Wow. I was in love already, or at least I had the biggest crush in the world.

But then, so did every guy in the office. One guy I knew from our department approached her, but he was shot down in flames, just like every man before him. I wasn't going to let that happen to me. I was going to be different. I was the one who was going to break the ice, and get a date with Tawny.

Obviously, the direct approach wouldn't work. I needed to be more devious than that. How about sending her an email, or writing a note? Well, it was pretty certain that other guys were doing that too. I needed to stand out from the crowd.

I was watching her at lunch again today, and I noticed something: for the third day in a row, there was this one brunette chick who was eating lunch with her. When I watched her go for coffee later in the day, the same chick was with her again. Bingo! I had it: I would get to her, by going through her friend.

 

Now I started to do some research on her friend, who's name turned out to be Veronica. I kept my eye on her, and one day soon after, when I got to the cafeteria, Veronica was sitting there alone. I knew from my daily observations of Tawny, that she was in a meeting. Perhaps they had lunch brought in, or they were running late. In either case, this was my chance.

"Do you mind if I sit here?" I asked.

"No, not at all" said Veronica, moving her tray aside.

I sat down, and put my napkin on my lap, so she would see that I had manners.

"Hi, I'm Craig" I said.

"And I'm Veronica" she replied.

"I know" I said.

"Oh really?" she said, in a flirty tone of voice.

Bingo! She thought I was interested in her. And under normal circumstances, I would have been. But not now. I had my sights set on a higher standard: Tawny. But if Veronica was a good friend of hers, then she would be a great asset for me.

We had lunch, we had a friendly chat, and things were going great.

"Maybe I can have lunch with you again some time, or coffee?" I said.

"That would be very nice" she said. "You can call me at extension 1959."

"I know. I looked up your number already" I replied.

She loved it. It was flattering that a guy was interested in her like that. And so, my new friendship with Veronica started.

 

We would always say hello if we passed each other in the hall. I would stop by her desk on the way to the copier (after passing by Tawny of course), and stop in to say hello. Or I'd bring her a cup of coffee. Little things like that.

In turn, she invited me to sit with her at lunch ever now and then, when I arrived later than she did. Or she would sit down at my table, uninvited. Soon, word got around the office that we were becoming "an item". And then I must have built up enough trust with her, that I got the first invitation to go out with her and a few friends for lunch.

I rode with her, in her car, as we drove to a nearby restaurant. I sat down with her at a table, where we were joined by a few girls from the office, one other guy, and then the star of the show (as far as I was concerned): Tawny.

This was my first contact with her in a social situation. Now in reality, I wanted to ask her to marry me, right then and there. But I needed to keep up the appearance that I was after Veronica. You would not believe how difficult it was not to stare at Tawny, and to keep my eyes (and my attention) focused on Veronica. I wasn't ready to make my move yet. I needed to be patient.

 

Things started to really roll. I started to see Veronica socially, as well as at work. We didn't make out or anything, just hanging out, talking, having a good time. And this meant that I was also able to hang out with Tawny some more, outside of work. She was getting to know me a little, and I was getting to know her, even as I sat there on the couch, with my arm around Veronica. Tawny knew me now, and I think she liked me as a person. Now I had an edge over everyone else in the office.

Now came the hard part: I had to 'break up' with Veronica, so that we weren't a romantic item anymore, but we had to stay friends, so that she could help me, and I wouldn't look like a total jerk to Tawny. From all the things we had talked about over the past months, I had enough little things which I could use to tell her. I noticed her copy of Cosmo opened to a "relationship test". I scanned the questions while she was using the bathroom, and I smiled. It was perfect.

"Hey, lets take this relationship test" I said, when she returned.

"I thought guys didn't like these things" she said.

"A terrible myth" I said.

"Okay" she replied.

We went through the test, and to my satisfaction, we ended up matching only six of the fifteen questions. That led to a difficult talk, in which we talked about long term goals. And to my delight (although I had to keep a sad face on), we decided that we weren't cut out for each other.

"Now I know this sounds so cliched" I said, "but even though we're not going to be in a relationship anymore, I really do want to keep you as a friend. I treasure our time we've spent together."

"Really?" she said, with tears in her eyes.

It was tearing up my eyes to have hurt her feelings like this, but I *had* to. This was my way to end up with Tawny.

 

* * *

 

After letting things simmer for a week, I started joining Veronica for lunch again in the office. Or I asked her to go to a movie with me, just as a friend. We resumed our relationship as 'buddies', and now was the time for me to strike.

"I just feel *so* alone" I told her, as we watched a movie over at her place. This was something we did every now and then, just for fun.

"I know. Me too" she said.

"I've met someone at the office who I think I'd like to ask out" I told her, "but I'm too shy to do it. Can you help me?"

"You? Shy?" she said. "You're always confident and forward."

"Well how about scared then? I don't like to fail, and get shot down cold when I'm asking a woman out. I've met someone who I *do* want to ask out, but I just don't know how to ask her."

"Who is it?" asked Veronica.

"I hope this doesn't make you feel bad, but it's your friend Tawny. Ever since we've broken up, I've been thinking of her as someone really nice I've met, who I would like to get a chance to know better. But all the guys in the office say she is cold as ice, and that she has shot down every single one of them who has asked her out. So you see, I want to try to get to know her better, but I don't want to be just another guy who she brushes off. Can you help me?"

Veronica had that sad sympathetic look in her eyes. Bingo. She was going to help me! My months of hard work and planning had paid off. And I made sure to make it sound like I was only interested in Tawny after our breakup. And I stressed that I wanted to start slowly with her. I'm sure most guys must come on really strong with her, so I wanted to look gentler, and different.

 

"You don't want to date her" she said. "It wouldn't work."

"Why is that?" I replied.

"There is a good reason whey Tawny doesn't date men at the office."

"And why is that?" I asked.

"It is because she doesn't date men."

What? My perfect blonde goddess was a lesbian? How could that be! No! But I had come this far, I wasn't about to give up.

"Look Veronica" I said soberly. "She is just the nicest person I've ever met, except for you. And she does something to me when she looks at me. It is like a feeling of electricity. I hardly know her, but now that I've noticed her, I feel like I was made for her. I have *got* to give it a try with her, no matter what it takes. Please, can you talk to her, and ask her if she would be willing to go out with me just once? If it isn't right for us, then I'll forget it. But please, can you help me?"

"All right" she said. "I'll talk to her, but I can't make any promises."

"Thank you so much Veronica. You are a true friend."

I felt like crap at how I was using her, but it was a necessary evil. And it had worked. She was going to talk to Tawny for me, and I had a chance!

 

* * *

 

A few days later, Veronica called me on the phone after work.

"Craig? I spoke to Tawny for you."

"Thank you!" I said, trying not to sound too excited. "What did she say?"

"She told me that she is willing to give you a try, for one date, but it has to be on her terms. Come to my house on Saturday, at 2:00 in the afternoon, and I'll prep you for your date."

"Thank you Veronica. Thank you so much."

"Don't thank me now" she said with a giggle. "Wait until Saturday is over."

I had no idea what she meant, but I didn't care. I was going out with a date with Tawny!!!

 

The next few days crept by so slowly. I went on a harsh diet, I worked out for two hours a day, and did my best to be as good looking for Tawny as I could. Saturday was pure torture. I couldn't sleep the night before, I couldn't do anything, because I was too excited.

But finally, it was time to prepare. I picked out a good "first date" outfit, and got dressed. I looked at myself in the mirror, in my casual dress shirt, my khaki pants, my polished brown shoes. I looked good. I went to the florist and bought to bouquets: one for Tawny (red roses), and one for Veronica for helping me (carnations). I got in my car, and I drove to Veronica's house.

I had no idea what the plan was. I just knew that she would 'prep me', then I would go off and be on my date. I guessed she'd give me some background info, and tell me what to do or not do on the date. Whatever she said, I vowed to listen carefully, so that I didn't do anything to blow it with Tawny! I had worked hard, and I wasn't about to mess this up now.

I went knocked, and waited on the doorstep. Veronica opened the door, looked me up and down, and told me I looked very handsome. She give me a light kiss on the cheek as we hugged each other. Then I went inside, and she motioned for me to sit on the couch, across from her.

"We need to talk about Tawny" she said. "Now you've had time to mull over the fact that she is a woman who feels attracted to other women. Do you really understand that?"

"Yes" I said. Actually, that sounded kind of hot, Tawny with some other chick. As long as *I* got to be the third part of the trio! But I didn't dare say this to Veronica.

"And since she is attracted to *women*, that is what she wants to date. Right?"

"Right" I said. Made sense.

"But you are a man" she said. "So we have a problem. How can we then have you go out on a date with a woman who is interested in other women?"

"I don't know" I said, "but I'm sure you have a solution."

"I do" she replied, now smiling broadly. "Since she wants to date a woman, and you want to date her, the only logically solution, is to turn *you* into a woman."

I was stunned, not ready to be told that!

"Um, what do you mean, turn me into a woman?"

"You'll make a very cute woman. I'll dress you up. Put you into panties. Put you into makeup. Give you a wig. Make you look like a chick. Then I'll teach you how to walk in high heels, how to carry your purse, and then you can go out with Tawny."

"I don't know...." I said.

"Yeah, she said you'd never go for it. I guess it was a bad idea. Thanks for coming over tonight though. She'll be disappointed that you wouldn't go through with it."

"Now just hold on a second" I said. "Isn't there some other way?"

"I'm afraid not dear. I discussed this with her at length. She is expecting you to meet her tonight, dressed up as a girl, and she is excited about it. If you show up as a guy, well, as you told me you were afraid, she'll shoot you right down. This is your only chance. Become a girl and date Tawny, or go home alone. And by the way, you'll make her mad at *me*, since I had to twist her arm so much to get her to even do *this* to date you. I really stuck out my neck for you! You don't want to hurt me too, do you?"

"No" I said.

I was full of conflicted emotions inside. I couldn't go out, dressed up as a girl! But if I said no, I would have blown my one and only chace to be with Tawny. And I'd hurt Veronica's feelings, which I already felt bad about hurting from using her in the first place. There was too much at stake, and I had invested too much in this project. Like it or not, I had to go through with it.

"Okay" I sighed, giving up my fight. "I'll do it."

"I'm glad you've come to your senses Karen" she replied.

"Karen?" I asked.

"Yes" she said. "That's your new name, now that you're a girl."

I was Karen? That was a chick's name! How could that be me?

"Now Karen, as I prepare you for your date with Tawny, there are a couple of things to keep in mind. First of all, do not fight me, with what I tell you to do. I'm not in any mood to argue with you. If I tell you to put something on, or to do it, just listen to me. If you're going to argue, you can go home right now. Agreed?"

"Yes" I said.

"Secondly, that voice of yours needs some work. It is too deep, too gruff. Try to talk like a girl, since you are one now."

"Is that necessary, telling me that I'm a girl, and calling me Karen?" I said, trying to sound less manly in my vocalization.

"Yes it is Karen. You need to get used to having people call you by your name, and you need to get used to the fact that you're a girl. So I will keep doing it. Not to rub it in, but to *help* you. Now tell me your name, and tell me what you are."

"I am Karen" I said in a shaky voice, that I tried to pitch even higher still. "I am a girl."

"There, that wasn't so bad? Now tell me again, and tell me that you are a *woman*."

"I am Karen" I said, my voice steadier this time. "I am a girl. I mean, I am a woman."

"Very good Karen. You'll get used to being a woman before too long. And I'm here to help you. I know it must be quite an adjustment. But stick with it. In no time, you'll think of yourself as being female."

I nodded my head, but I was unsure.

"Since you are a girl now Karen, go take a bath, and shave yourself. Your legs, your chest, and your underarms. I've already run the tub. It is full of bubble bath, and rose scented oils, so your skin will get nice and smooth, and you will smell pretty."

I was in kind of a daze as I got into the bath, with all the flower smells coming from the water. The room was lit only by flickering candles, which also gave off a flowery scent. I took the pink shaver, and went to work on myself. I felt so embarrassed to be doing this! Had I gone insane?

It took some time, since I had so much hair on my legs. It wasn't easy to shave my chest either, and I nicked myself near my nipple. And then I went at the jungle of hair under my arms. That was the hardest, because each little stroke would clog up the shaver, and I had to clear it out.

But finally, I had it all off.

"How are you doing in there Karen?" called out Veronica through the door.

"I'm almost done!" I replied.

"Make sure you clean out your hair from the tub when you're done" she said. "And then put on the cream you see by the sink. That will moisturize your skin, and keep it from itching after having been shaved. Put on some deodorant, and the bathrobe, then come to my room."

"Okay" I said.

I dried off with the pink towel, as the tub drained. There was a lot of hair, all over, and I had to wash it all out, and unclog the stopper. Then I used the lotion from the dispense by the sink, and rubbed it in all over. Floral scented again. I didn't like all these girlie smells on me! Even the deodorant was a woman's brand, and it smelled like baby powder. I put on the pink bathrobe, and left the bathroom behind me.

 

Once in Veronica's room, it was time for her to start dressing me. The first thing that she gave me was a pair of lacy black panties. They were super sexy, and very intimidating.

"What are you doing?" I asked, as she took a maxipad out of the box on her dresser.

"Putting in your pad. Something thick and even, to help hide that unsightly bulge between your legs, Karen. Plus, if you get your period tonight, your date won't be ruined."

With the pad in place, she handed me the panties, which I pulled on. I felt really humiliated and embarrassed. Here I was, with my former girlfriend, wearing black lace panties with a maxipad. She was calling me a girl. She was calling me by a girl's name. And now she was telling me about having my period. Not what I wanted to hear! All of this made me feel *weak* inside, in a way I had never felt before. It made me lose my libido, and the small rise I had gotten from seeing the black lacy panties was gone. I was small and limp now between my legs.

Maybe that was what she wanted though, because next came the girdle. It was white, and it looked quite intimidating. She handed it to me, and told me to pull it on. There was extra padding in the hips and in the seat, which she told me was to help reshape me.

"You don't have a classic 'hourglass' figure Karen" she said. "So we'll use an old classic technology that women have used for ages, to make themselves look instantly curvy. Pull it up all the way, and I'll lace it up in back."

I pulled it up to the top of my tummy. It was very tight in the crotch, not being made for a man. The fabric was stiff on purpose. It was intended to shape me, not to let me shape it.

"Now exhale, and hold it" she said.

I did as she instructed, and she pulled on the strings in back. Hard! I felt the girdle constrict on me. She moved to the next set of holes from the strings in back.

"Again. Exhale."

I did it, and she pulled it tight. Ow! I felt helpless, as bit by bit, the girdle clamped down on me, forcing my tummy to be flatter than it had ever been before, reshaping my flesh to force curves into being where none existed before. And did I mention that it made it a little harder to breathe?

"There" she said. "You'll look a lot cuter now Karen."

"I don't feel cute!" I gasped, trying to get used to the feeling of having such a tight form-shaping garment on me.

"Next, you need to enhance your bust, because you are a very flat-chested chick. That's why I got you these."

'These' were large fake breasts, bigger than hers, bigger than even Tawny's.

"Do I really need those? And if I do, must they be that big?"

"Now Karen, you promised me not to argue. And yes, you do need them. With the size of your shoulders, these will help keep people's eyes attracted elsewhere. Especially men. Do you want them staring at your face, or at your boobs?"

"My boobs, I guess" I said, having not yet thought about that fact that if I went out in public as a woman, I'd have guys scoping me out, as they would any other chick.

"Oh look at you, you're blushing!" said Veronica. "What a shy, modest girl you are. But don't worry, after tonight, I'm sure you'll learn to loosen up."

"I need a drink" I said.

"An excellent idea, girlfriend!" said Veronica, as she put the fake boobs into position.

They were covered with a special glue on the back, to hold them in place, which felt wet and cold against my skin.

"Hold them still, and I'll be right back" she said.

I put my hands over them, and they were huge. I held them in place as they dried. Looking down, I saw big boobs in my hands, a figure with curves, and a tight crotch lying almost flat, with the maxipad and the thick fabric of the girdle pushing my natural bulge down almost flat.

I felt even more intimidated now than before. Seeing what looked like large women's breasts lying on my chest, in my hands, made me feel very strange. Like my manhood was being taken away from me. She *was* turning me into a woman, and I felt powerless and vulnerable. Was this what real women felt? How could I go outside in public like this? People would see me with boobs!

I was so happy when Veronica returned to the room with two large glasses full of margaritas. I took a big sip off of mine, and felt the wave of intoxication roll through me, sending a shiver up and down my spine. I took another deep sip.

"Look at your chest Karen" said Veronica. "Doesn't it look better now?"

I had let go of my boobs when I took the drink, and they stayed in place when I let go. The glue had dried. I could feel the weight of them on my chest. I almost freaked out seeing them hanging there, with the realistic nipple, and the wide dark ring of color around it.

"Lets get you into a bra" she said.

I took the black lacy push-up bra from her, and tried to put it on. She laughed as I fumbled with it in back, trying to get the stupid little hooks into the loop things. When I finally got one in place, she told me it was in the wrong row, and I had to do it again!

But finally, I got it right. I looked down. I had cleavage. Oh god. Me! With cleavage! My fake boobs were gently cupped and supported by the black bra, with the triangles of material forming a V where they met in the middle. The stiff nipples made bumps that showed through the front. And the weight of my boobs made the straps dig into my shoulders.

The bra wasn't much, but it felt *so* constricting! It was more intimidating than the girdle had been. I felt like I was trapped, and I had to get away. This was terrible! What was I getting myself into? I had to picture Tawny in my mind, to remind myself why I was even doing this! Do you realize how awful it felt to prepare for a date, by getting boobs bigger than the girl you wanted to be with? I was so hyperaware of my boobs. They felt like they were in the way. They rubbed against the inside of my arms. I felt like I wasn't myself anymore.

"Before we move on, we need to do your nails" said Veronica.

"Nails?" I said.

"Yes" she replied. "Sit on the edge of the bed, and put your feet up here. I'll start with your toes."

She was painting my toenails bright red. I felt that awful tingle in my groin again, that feeling of intimidation and powerlessness. She put cotton balls between my toes, to space them apart, and she told me to hold still so they could dry.

Now she put some acrylic glue-on nail extensions onto my natural fingernails, and held each one in place for a few moments to let them dry. Then she took out a nail file, and shaped them into ovals. She wiped them off to get rid of any dust from the filing, and then she applied a base coat and a second coat of the same bright red color that my toes now had, and then finally a clear topcoat. In between each coat, I had to hold my fingers out, and let them dry. I felt *so* terrible! I had long painted fingernails now.

But we were far from done, and I knew it. She was turning me into a woman, and I had to go along with it. I was getting a little chilly, with so much exposed skin, so I was glad when the next thing she put on me was knee-high nylon stockings. They were a tan color, with a wide elastic band at the top to hold them in place. I felt kind of dirty now, in a black bra, stockings, girdle, panties, and painted nails.

I was *so* scared that she was going to make me wear a short skirt or something, so it was a monumental relief when she went to her closet and returned with blue jeans. I was so happy, I wanted to cry. Well, almost. I wasn't quite a woman yet!

"I knew your size from when we dated" said Veronica. "I went to a thrift shop, and found a pair that should fit you, now that you have your girdle on. I don't know, these might be a little tight."

I stepped into the soft, broken in pair of blue jeans, and pulled them up as if they were just like the ones I normally wore. Wrong!

First and foremost, my jeans didn't get narrower at the top, like these did. They were designed to hug a woman's curves, and with the tight girdle constricting my form into a feminine hourglass, they fit me that way. Secondly, my jeans had lots of room in the crotch, but these were tight, right up against me. Between the jeans, the girdle, the pad and the panties, there was no bulge in sight. I must say that *this* intimidated me even more. It was as if I did lose my manhood.

The jeans were bell bottoms, which allowed enough room for me to put on the next item: a pair of boots. They were black, coming up midway between my ankle and my knee. But they had a very pointy toe, a bright metal buckle, and a four inch high spiked heel. And they were tight, since they were narrow, and my foot was quite a bit wider than them. Looking down at my lower half....and having it look like it belonged to a chick, that just floored me. I thought I felt weak before, but this was *worse*.

I didn't protest as Veronica threaded a wide white belt through the loops in the jeans. It had a large buckle shaped like a butterfly in the front, and drew attention to how I narrowed up there, accentuating my newfound curves.

I was scared she'd give me some frilly lacy top or something, but again I was relieved that instead, she had selected a turtleneck sweater. It was black, with long sleeves. I put it on, and it felt really strange to have to pull it over my boobs. It felt to short for me, just barely reaching my jeans. If it pulled up at all, my bellybutton would be exposed. I guess I had seen a lot of the hottie babes dressing like this, but it felt *so* wrong for me!

I looked in the mirror, and I almost passed out. The turtleneck did a couple of things for me. First, the long neck hid my adam's apple, so you couldn't see as plainly that I was a guy. Secondly, it was tight, and it made my boobs look huge. Every guy would be staring at me, all night long. I was starting to *feel* like a woman now, and I was just shaking.

 

"Lets work on your hair next, Karen" she said.

Veronica went to her closet, and returned with a wig. The hair was long, wavy, and colored red. She showed me how to put in on, and how to secure it so it didn't fall off. Long hair fell down the side of my face, and the back of my neck. I was so intimidated now, that I couldn't even find the strength to speak.

Veronica pulled my hair back into a ponytail "for now", so she could start to work on my face. She began by putting on some cream stuff that was colored like my skin.

"What's that?" I asked.

"Foundation" she replied. "Hold still. Don't talk."

She used all sorts of brushes with different powders on my face after the foundation dried. Some was flesh toned, some was red in various shades. She outlines my lips with some kind of a pencil thing, then used a brush to put shiny stuff on them. She used pencils and powders and creams around my eyes, and then one of those brushes with the black stuff girls put on their eyelashes.

Then she put stuff on my eyelids, some kind of pencil thing on my eyebrows, and she wasn't done yet. She clipped earrings onto the lobes of my ears, and they kind of pinched. They were big loops which dangled there. When they brushed up against my skin, they felt cold, which was weird and different.

Next, she hung a necklace around my neck. It was silver, with a butterfly inlaid with little shiny blue and green stones. She dropped it down inside my sweater, and I felt the butterfly come to rest between my boobs. Nobody could see it, but I knew it was there.

She put a couple of rings onto my fingers. One was gold, with a little row of emeralds (or green stones anyway....what do I know about jewelry?). The other was silver, and had what I thought was kind of a large butterfly on it.

"What's with all the butterflies?" I asked.

"You're a girl who loves butterflies" she replied. "And so does Tawny, so you'll be a big hit with her. Trust me."

At this point, what choice did I have?

Veronica had a ladies watch, which she put on my left wrist. It had a very narrow band, and the face was way too small. On my right wrist, she put a strand of pearls. She pulled my shirt back down, since it had rode up a little, then walked behind me. She released the long hair from my wig from the ponytail, and it fell all around me. If I moved, the hair moved, ticking my neck, getting in my eyes, making me feel scared.

"Are you ready to see the new you, Karen?" she said.

"I guess so" I replied.

"Good. We're almost ready."

"Almost?" I replied.

"Yes. A few more little touches to go."

She took out a pair of glasses, which were oval shaped, kind of like a cat's eyes. They had thin dark frames. She put them on me, took them off, made an adjustment, and put them on again.

"I don't need glasses" I said.

"I know. The lenses don't effect your sight. They are just for looks."

Then she took out a small purse, with a long thin strap. She told me to put it over my shoulder.

"Now you're ready to see yourself, Karen. Walk over to the mirror."

I stood up and took a step, and almost went flying on my face. I had forgotten about the high heels, and if I hadn't caught myself, I would have been laying on the floor. I took small, wobbly, cautions steps over to where Veronica was standing. She laughed at me.

"Girl, you're going to have to learn how to walk in heels. But first, what do you think?"

I looked in the mirror, and I was floored. I explained how as I had undergone the process of being turned into a woman, I felt less and less of a man. I explained how it made me feel powerless and weak. Well, now seeing the full package, it was like I got hit over the head.

I had long hair. I had a pretty face, with makeup that gave me shiny red lips, flirty eyes, and a hint of glitter on my cheeks. I had big boobs, curves, high heels and pointy toes....the purse over my shoulder was like the final touch of it all. I *was* a woman now. You couldn't tell. Really. My own brother wouldn't recognize me. If she had used a knife to clip off my male genitals and throw them in the garbage, I wouldn't feel any worse than I did a that moment.

I just stared at myself as she sprayed me with perfume, and started putting things into my purse, like extra makeup, a small coin purse, and a couple of tampons.

"In case you start your period, and your maxipad isn't enough because you're flowing too heavily."

That was so gross, I didn't even want to think about it.

"Now follow me" she said. "Let me show you how to walk in heels."

She led me to the livingroom, and gave me a demonstration. She made it look so easy! She went over the basics, and told me to practice while she got something ready for me. I walked back and forth, sat down, and stood up. Over and over. After a dozen times, I finally felt like I wasn't about to topple over at any moment, but I was far from graceful. I kept at it though. She was gone an awful long time, as I tried my best to get good at walking in heels.

"Where were you?" I said, when she finally returned. She was carrying an old hand towel.

"I was masturbating" she said, holding the towel up. "I've soaked this with my juices. Now come here, and hold still."

I was shocked. The thought of a chick doing herself was wild, and normally would be a turn-on. But not at this moment! I walked up to her (showing my growing mastery of moving around in heels). She held the rag up to me, and it was the familiar odor that a woman exudes from between her legs. She took it, and started wiping it on the crotch of my jeans.

"What are you doing?" I asked, feeling uncomfortable for her to be rubbing me down there.

"When you get aroused, you get wet, your juices start flowing inside your vagina" she said, as if I really was a girl, and she was teaching me about my body. "Now when Tawny sees you, you'll smell as if you're getting wet from being with her. She is a lesbian, so this will really turn her on. You'll have to trust me on this, but it's true. Now I've also put a little bit of my juices on this cotton swab, which I'm putting into a ziplock baggie. When you're out to dinner tonight, make an excuse, go to the little girl's room, take this out, and give yourself a booster coating of it. Tell her she's getting you all wet, and you're golden."

"But how can I go with all this on? I'd have to remove the girdle to go."

"Well then Karen, I guess you'll have to hold it all in, won't you?"

 

Now she made me practice sitting. I had to keep my legs crossed, or keep my knees together, and my ankles together. I was never to show my crotch.

"Pretend you're wearing a skirt, and you don't want everyone looking up at your panties" she said, trying to be helpful. In this outfit, it wouldn't take much to imagine myself in a skirt.

She worked on me, telling me how to act like a girl. She told me that Tawny would probably be the more dominant one in a relationship, so I would have to be the more feminine one. I had to be passive, and let her make the decisions.

"Let her treat you like a lady. She'll want to hold doors open for you, and things like that. Let her. It makes her feel good that she's treating you like a lady. You might even think of deferring to her judgment on things. Like when she asks what you want for dinner, ask her to order for you."

We worked on my movements, my posture, how I sat, how I stood. Time flew by, and before I knew it, there was knock on the door. Oh no, someone was going to see me like this!

"Who's that?" I asked, really scared.

"Tawny" she replied.

I was dumbfounded, and I froze. I guess I forgot that *she* was going to see me like this.

"Don't forget that you're a girl now. Act like on. Talk like one. *Be* one, if you want to score points with her" said Veronica. "And for god's sake, if you two end up making out, whatever you do, do *not* try to penetrate her with that *thing* between your legs. If you even try, she'll never talk to you again. You're a girl now Karen. You're a woman. Remember that!"

I stood up, pulled my sweater down so none of my tummy was showing. This was so much to take in at once. The door opened, and there was Tawny. I never saw her looking so hot before, and my heart just melted. She had on black pants, shoes with pointy black toes and high heels (sort of like me!), and a greet top. The kind with those tiny little straps over the shoulders, so small they don't hide the bra straps. It made a deep V, showing off her impressive bust. Mine was bigger, but hers was *real*.

"Tawny, this is Karen" said Veronica. "Karen, I believe you know Tawny."

She walked over to me in a sexy strut that I could only admire. It would take me years before I could move like that in heels. She came right up to me, her boobs pressed up to mine. She put her arms around me, and kissed me on each cheek.

"You look very pretty" she said.

I wanted to die. I was in heaven, because the most perfect angle ever created had just kissed me. She was here to go on a date with me! But I was dressed up like a girl, and she had just called me pretty. My hormones were crying out to my manhood, trying to make him get hard and erect. But with everything so tight in my crotch, it was impossible. I was limp, getting no rise at all from having her brush up against me, put her arms around me, and kiss me. I wanted to die.

"You're very pretty too" I said.

"I like your boots" she said. "They really make your outfit."

"Wow, thanks" I said. "I like your *everything*. You have a great style."

"That's so nice of you to say that, Karen" she replied.

She was looking me right in the eye. It was so massively exciting to have her flirting with me, and looking me in the eye. But she had just called me 'Karen'. I was a girl to her. A girl!

 

"These are for you" I said, presenting her with the roses, which Veronica had put into a vase with water, while I had been shaving my legs in the tub.

"Aw Karen, you didn't have to do that. Thanks!"

That earned me another hug. Our tummies were touching, as were the crotches of our pants and our boobs. She kissed me very lightly on the lips, so as not to mess up either of our makeup. It sent shivers all throughout me. I had never been kissed like that before. Just a simple touch from her, and I was going wild all over inside.

 

"You two lovebirds had better get going, so you don't miss your reservation" said Veronica.

"Thanks for setting this up" said Tawny. "This is the best blind date I've ever had."

"Yes, thanks for everything" I told her.

"Bye-bye girls! Have fun tonight!" she said.

Veronica watched as Tawny took my hand, and we walked down the driveway.

"Why don't you drive?" I suggested.

I did it party because Veronica had told me to say it, but also party because I didn't know if I could control a car driving with these high heels on. Tawny led me to her bright red VW Jetta. She opened the passenger door for me, and I got in. Once safely seated, she shut my door, and walked around to hers. She was so hot. I couldn't believe I was on a date with her! But I couldn't believe that I was doing it as a woman.

 

We talked as we drove. Since we had gotten to know each other a bit when I was dating Veronica, we were able to talk right away. Not once did she even allude to the fact that she had known me as a guy. She treated me as if I had always been a girl, and that all the times we had met before, I had been a girl then too. Even when we talked about work, she acted as if I was one of the female employees.

"I'm glad you dressed appropriately for our first date" she said. "The last chick I dated came to the first date in a long skirt that made her look like we were heading for a wedding."

I laughed.

"I have to admit, I got some advice from Veronica. She's better with fashion than I am."

"I'd love to start teaching you" said Tawny.

Now that was an offer I would accept, as much as I disliked the subject matter. Anything to spend time with her!

"Sure" I said. "I'd love to. Nothing like being taught by a master of the subject."

"Why you little flirt!" she said. "Flattery will get you everywhere."

She giggled, so I tried my best to give her a girlish giggle in reply.

 

We arrived at the restaurant, a casual Bistro. Tawny found a good parking place, and we only had to walk two blocks to get inside. This was my first time walking in public, dressed as a woman. We got lots of stares as we held hands. I knew how every guy at work was always looking at Tawny, and she must be used to it by now. But I felt flushed and red, as I felt the burning stares of men and women alike. It was a relief to go inside.

"Ladies, let me show you to your table" said the man at the door. I was instantly accepted as a lady right away. I didn't like this at all! But I guess being seen as a man would have been bad too. A real no-win situation, if I ever saw one. The only thing pulling me through, was the fact that I was on a date with Tawny. I could tolerate anything to be dating her!

We chatted, then ordered a bottle of wine from our cute young waitress. I don't know if I should have been surprised about it, but Tawny was scoping her out.

"She had nice boobs, don't you think?" she asked me.

"Not as nice as yours" I replied. "You are perfect, if you ask me."

"What did you think about her shoes?" asked Tawny.

I sensed that this was a test. I knew that real chicks were into clothes a lot more than guys, and knew fashion and stuff way better than we did. To tell you the truth, I didn't even look at the shoes our waitress had on. I knew nothing about them. But I didn't want to look stupid either. Veronica had warned me to act like I was a girl. So I did my best to make something up.

"Well, you know" I said, noting the discomfort I had in my feet from my narrow boots, "you've got to wear something comfortable when you work on your feet all day. Kind of limits you, don't you think."

"I'm so glad you really understand" said Tawny, moving her chair closer to mine. And from then on, she treated me a lot more like a date, and less like a friend. I guess I had impressed her with acting enough like a chick, and she got closer to me. I liked it!

 

Dinner was fun, then we went for a walk, hand in hand down the street. My feet were killing me, but I just kept focused on *her*. We stopped at a little photo shop, and had our picture taken together. We got two printouts, one for each of us. Afterward our walk, we drove back to her place, where she invited me to sit down on the couch.

"I have something I'd like for you to watch" she said.

"Sure. I love movies" I replied.

Tawny put a DVD into her player, and turned the TV on. She pushed a few buttons on her remote control, and the screen lit up. The show was called "Horny Housewives", which sounded exciting to me!

The show started, and Tawny sat down, right next to me. She put her arm around me, and snuggled close. It was the best feeling I ever had in my entire life. In the tightness of my pants, my manhood wanted to get hard, but there was just no room, so it really hurt. But I worked through the pain. You gotta do what you've gotta do!

The film looked cheaply shot. And in a few moments, it was apparent that it was no Hollywood film, but a porno flick. The plot was pretty silly. Once woman was doing housework, wearing a skimpy form fitting yellow dress, with her hair up inside a bandana. There was a knock at the door, and it was another woman, from down the street, asking to borrow two eggs.

They started talking, then sat down, and next thing you know, they're kissing. The first chick takes off her bandana to reveal her long sexy hair. And they start making out even more.

Soon, they're taking each other's clothes off, sucking on and pinching each other's nipples, and then they're getting completely naked. The first chick goes down on the second one, and there's lots of fake moaning. Then the second one does the first one.

I'm watching this, and while it's no Oscar contender, it is *really* hot to see two gorgeous chicks like that going at each other. It makes me realize that this is what Tawny wants to do with *me*, and it made me go crazy inside to imagine having that with her!

I thought the film would end, but instead, things got even more intense with the two chicks. One of them takes from her purse this white thing, which is about ten inches long. The second one spreads her legs, and the first chick starts to insert it up into her pussy (after playing around a little to get it going in)! Then the second one mounts her, so that it's going into her pussy too. Wow. They're doing each other with this white rod, and my mind is going crazy, although my manhood just couldn't get hard from the tightness of my pants.

In the end, the two of them snuggle, talk, then giggle as the dress back up, and go off to their lives. Wow. They had an affair, then got back to their housework. As the first chick is putting on her bandana again, she has this wicked smile, as the camera fades out.

I couldn't get the images out of my mind. It was really hot. I turned to Tawny, who whispered into my ear.

"That's what I want *us* to do" she said.

The next thing I knew, she started to kiss me! Just like the girls in the film. So I kissed her back. I was hugging her, squeezing her, and kissing her. I guess I got a little too rough though, because she backed off a bit.

"Remember love" she said, "*you* are the woman in our relationship. I will lead, and you will be passive."

That was all right with me, as long as I was making out with her. I backed off, and let her set the pace. And before long, I was rewarded. She started to take my clothes off, and then I started to take off hers!

I was holding her, feeling her bare chest rubbing up against me. Men at the office would have killed for a chance to see her naked, and here I was holding her! She wanted me!

"I want you to go down on me, love" she said. "Like in the film."

"Whatever you want" I replied.

I was wearing just my bra (with the fake boobs of course), and my panties. I got down on my knees as she laid on the couch, and I did her with my tongue. She guided my hands onto her perfect breasts, and I gently massaged them like the chick did in the movie, as I used my tongue to pleasure her clit. She really enjoyed it, laying there moaning. I gave her an orgasm! How lucky I felt to be the one doing this with her!

When she had enough, Tawny used her hand to push my face away from her sweet pussy. I had to wipe the drool off my chin. I was grinning ear to ear. Now it was my turn.

She pulled off my panties, and I sat on the couch.

"Spread your legs wide open for me Karen," she said, "so I can play with your clit."

I did as she asked, and she lowered her head.

I expected her to put me into her mouth, but I was still limp. I guess having my private parts crushed by the tight pants for so long, it would take a little while to recover. It was still sore down there a little.

Just as I had used the tip of my tongue to play with her clit, she started to use the tip of her tongue to play with the head of my limp member. She was acting as if my manhood was just an enlarged clitoris! And she was playing with my fake boobs, as if they were real. This wasn't what I had envisioned.

But then I decided that she must be saving my orgasm for later. So I played along, pretending to moan and enjoy it as she did. It really bothered me that I was never able to get it up though.

 

Finally, she stopped what she was doing. She stood up, sat on my lap, and we started kissing again.

"Oh Karen, I think I'm falling in love with you" she said between smooches.

I kissed her back. I was already in love with her, and I told her so. We were touching each other, and I could feel so much of her body with mine. My hands wandered all around her perfect form, and I felt so privileged to be the one who was doing this to her.

Tawny stood up, and walked over to the end table by the sofa. She opened up a drawer, and removed an object. I gulped. It was a flesh colored dildo, sort of like the one in the movie. Except that his one was very realistic looking, just like a man's anatomy, except for the fact that it had a head on both ends! I knew what she wanted now.

I was very slow and playful at first, teasing her before I inserted it into her wet opening between her legs. I moved it in and out with a slow gentle rhythm, trying to go a little deeper with it each time. I think she came again, at least a couple of times.

After a while, she took it out of my hands.

"Stand up, Karen" she said.

I complied of course.

"Turn around. Put your legs wide apart, and lean over the couch."

I could see what she wanted, and for the first time, I was scared. She wanted to make a real woman out of me! I was almost crying as she started to play with the dildo, using the only opening I had between my legs: the one behind me.

I gasped, feeling not quite a pain, but not quite a pleasant feeling either, as she worked it in, and it filled me up inside. She pushed it in, deeper and deeper. Oh no! She was doing me! This wasn't supposed to happen!

Now she let got of it, but it was still stuck inside me. I felt her heat as she got nearer. She impaled herself on in, and slid down until her groin in the front was touching my butt. It was almost as if it was a man doing me from behind.

She started to build a rhythm, rocking back and forth behind me. I felt helpless as she drove it into me, pulled it out, and made me feel things I didn't want to feel. Between the overwhelming sense of excitement from being naked with her, to the vulnerability of having her penetrate me for the first time, I was just floating, as my brain tried to reconcile all of the conflicting feelings that were swamping me.

 

When she was finally done, she pulled it out gently, and handed me my panties. I put them on, and we laid together on the couch, snuggling. I was whimpering. I felt like a girl, and she had done it to me. We fell asleep in each other's arms.

 

* * *

 

When I woke in the morning, Tawny was gone. She left me a note though:

 

Dear Karen,

Last night was wonderful, babe! You are the best lesbian lover

I have had in a long time. I had to go to the gym to work off that dinner.

Feel free to fix yourself breakfast. Lock up when you're done. I'll call you soon.

 

Love Tawny.

 

 

I didn't stop the think that it was odd, that she didn't say that she'd see me Monday at the office. I had a mix of repulsion over what we had done, and attraction to this perfect woman. I felt an inner need to be with her. I *had* to be hers. And she *had* to be mine.

 

She didn't call me again that weekend, but I figured I'd see her Monday. And first thing, as I came to her cubicle carrying cups of coffee for the both of us, she looked up at me, and gave a faint smile.

"Oh, hi there Craig" she said.

Her tone was not that of a loving partner, just an acquaintance. I was mystified.

"Hi Tawny, how was your weekend?" I said.

"Just fine. I had a hot date. Is that coffee for me? You shouldn't do that you know. I can get my own coffee."

"I brought it for you. Cream, no sugar, just as you like."

"How did you know I like my coffee that way?" she said. "Have you been spying on me?"

She had ordered her coffee that way for desert. She knew that I knew! Why was she treating me like this? I excused myself, and made a hasty run to Veronica to ask her opinion.

"It's quite simple" she said.

"What?" I replied, dying to know the answer. "She was so nice and loving on our date, but now she's treating me like she did before. What's the matter? Did I do something wrong?"

"No, from what I hear, you were wonderful. But you have to realize: at work, she sees you as 'Craig'. A guy. Just another guy after her. She likes you as Karen. As Craig, you're nothing. As Karen, you are her date."

"So you're saying that for her to give me any attention, I need to be Karen?"

Veronica just nodded. I was exasperated. What good was it to go through all that trouble for the date, if it didn't even win me any points, unless I became a girl again for her? This was messed up, and as I walked to my desk, I swore that I was through with her.

But when I opened my briefcase, and looked at the photo of use together, my heart just melted, all over again. I would become Karen again, just to have another date with her.

 

Fridays were casual day in the office. I tried something daring, which was probably stupid, but I had to give it a shot. I went to the mall, and bought a woman's shirt. A 'tunic' the salesgirl called it, but I didn't know the difference. It was something that was definitely a girl's top, but with jeans on, I could get away with wearing it in the office. If anyone called me on it, I'd tell them that it was a gift from my mother, and I was wearing it to make her feel good.

I went over to Tawny's desk, and she looked up at me with a top on that was definitely made for a woman. Her smile wasn't the cold "buzz off, buster" look from Monday. It wasn't quite her "I love you Karen" smile either, but it was closer to that. And she was a lot friendlier to me.

After our meeting, word came down from Veronica that Tawny wanted to have another date with me....as Karen again.

 

On Saturday, Veronica got me all dressed up again for our second date. This time, I had on a whole new outfit. This time, I wore light colored nylons on my legs. And then, the dreaded skirt. It was a flowing yellow wasp-waisted skirt, with a stylized print that reminded me of sunflowers.

On top I wore a white cami, which had thin straps that didn't even cover up my bra straps. The V of the neck was trimmed in a lacy fabric, and it felt so skimpy, so girly. But then over that, I had a white blazer, with an embroidered dragonfly that was about five inches wide. It seemed huge to me, but Veronica assured me it was a nice touch on my outfit.

For shoes this time, she had a pair of white sandal style shoes, which thankfully didn't have much of a heel. Instead of one strap going across my foot like normal sandals, there were three of them, thin, with little buckles.

I looked at myself in the mirror. I didn't feel very confident in this outfit! My legs shoes. I felt naked. I was wearing a skirt. You could see the lacy trim from my cami. I didn't want to go out in public like this! But the thought of being with Tawny overrode my sense of fear. I was going out with her again.

 

This date was even better than the first. We talked, we laughed, we had a nice dinner, we saw a movie (and necked while watching it). We took a long walk together afterwards, and she told me I was very pretty.

We went back to her place again, and just as before, we made out. This time, without having my privates crushed by the tight jeans, I was able to get it up. But she never did enough to stimulate me. She played with my manhood as if it was a clitoris. She even called it that!

"My Karen, what a large clit you have. You should think about having that surgically reduced, so it doesn't get in the way so much."

Reduced? Surgery? That was enough to take the steam out of it, and soon it was limp again.

We made out, did all sorts of things, and then she pulled out the dildo again. She told me to put one end in my mouth, as I lay on the floor. I felt disgusted as she put it in, and I felt like gagging. She squatted on top of me, lowering herself so that it went into her hole. Here I was, with a real one, and she was making me get her off with this fake one, stuck into my mouth!

And then she did me from behind again. It went in easier this time, with less pain than before, but it had the same effect as the first time: when she was done, I didn't feel like a man anymore. It was as if she had taken that away from me all together.

 

* * *

 

Monday at work, I wore a pair of women's pants that I bought a store on Sunday. She noticed, and talked to me a little. So I got more daring. I bought other women's clothes that were androgynous enough to pass for men's, and started to wear them every day, just to get her attention.

I looked through all sorts of online shoe stores, until I found one that sold women's shoes in larger sizes. I got a couple of pairs for when we dated, and one pair which I thought could pass for men's. I used overnight delivery, so I could wear them with my tunic top on Friday.

"Nice shoes" said Tawny, "but you just wore that top last week, didn't you?"

Uh-oh. I didn't realize that you weren't supposed to do that. As a guy, you could wear the same outfit ten days in a row, and nobody would say anything. But it was clearly different for girls. I would need more tops so I didn't have her criticize me like that again. And I guessed that I would need more pants and things too.

Not to mention that I was shaving my legs now, to keep them nice for when we dated on the weekends. For the third consecutive Saturday, we got together again. This time, Veronica dressed me in something else different.

The top was an orange tank top, and with no blazer this time, I felt afraid that people would see my overly large shoulders. It also just barely covered my fake boobs, and I was also afraid that someone might look down my neckline, and see that they were indeed falsies.

The skirt this time was pink, with tiny pleats, and it didn't even come down to my knees. There was a ruffle at the hem, and it was frighteningly feminine.

"What about pantyhose?" I asked.

"Not with this outfit, Karen" said Veronica.

I felt naked. They'd all see I was a guy. I was even more scared. With each date, I was showing off more and more of my body. But without a feminine body to show off, it felt worse and worse to do it. And I felt silly wearing the gold colored high heel shoes. They had an open toe, and a very thin heel. I was frightened. Really!

And then Veronica said a couple of things that chilled me to the bone.

"This is the last time I'm helping you dress up, Karen" she said. "I have my own love life to worry about. You're on your own now. You need to go shopping, get yourself lots of sexy exciting outfits, and dress yourself up."

"But what should I get?" I asked.

"Read Cosmo. Read Marie Claire. Read Glamour. They'll tell you what the girls are all wearing, and you'll quickly learn how to put an outfit together. Read the whole magazine, and you'll learn a lot about girls as well."

"Okay" I said, shyly. The thought of going into a store and buying all these girl magazines was scary.

"And another thing Karen. If you really want to win over Tawny, you're going to need to make some lifestyle changes."

"Like what?" I asked.

"Well, she likes how you're starting to dress up in women's clothing at work. But you are too afraid there to really let loose. You still look like a man at work. If you want to show her you really love her, you'll start dressing up in something unmistakably feminine. Those boyish looks need to go. Either you're her girlfriend, or you're not."

I swallowed hard. How could I go into work dressed as a girl?

"And another thing. She really wants to touch your chest, and feel real boobs there. Your falsies look good, but look how you can't show them off. Imagine if this tank top had a lower neckline, and you could see real boobs underneath it."

"But I couldn't hide them at work if they were real."

"If you were dressing as a girl at work, would that matter?"

I paused to consider that. God, this was scary! This wasn't just a small change of style, this was an entire change of life she was talking about.

"You'll need to go on female hormones right away, so your body will be ready. Your skin will get softer, your real boobs will start to grow, but you'll get implants of course, so you'll be big."

"I don't know" I said. "I love Tawny, but I don't know if I can do all that."

"I'm not done yet" said Veronica. "There is one other adjustment you need to make. I know what she likes to do after you go down on each other. We had a fling one night when I was drunk, so I know. She told me she's using the only hole you've got. But if you want to win her over, you need to have the right pluming. Hasn't she told you she wants you to have your clit reduced?"

"Yes" I said, "but I didn't think she meant it."

"Well, she does. This is your last date with Tawny tonight Karen, unless you're willing to change for her."

 

It hit me like a ton of bricks. Tawny wanted me to turn myself into a *real* girl, if I was to have her. That really put a damper on the date. All the time, I had to ask myself if this was what I really wanted. Did I want to be myself, a man, alone? Or would I rather be a woman, a *real* woman, and be with Tawny? Did I want to become Karen full time? Was it possible that this was what Tawny really wanted?

I tried to ask her, but she didn't want to talk about me as a man. I was a woman to her, and that subject was off limits. All she would say was that she spoke to Veronica about it, and that Veronica had told everything to Craig. She referred to "him" as if "he" was someone else, and not me. I guess I really was Karen to her.

 

By the end of the night, I had made my choice. The time I spent with her was the most marvelous thing in the world. I knew that I had to do whatever it took for us to be together. As hard as it was, I would do it.

As a man, I had nothing. As a woman, I had everything. As a man, I couldn't wear the clothes I needed to get Tawny's attention. As a woman, I could. As a man, I was just a coworker. As a woman, I was her lover.

I know it may sound irrational to you, safely reading this from afar. But in my place, you might have thought differently. If you were in my shoes (which were high heels at the time!), holding Tawny's hand, seeing her smile, and wanting to be at her side for the rest of your life, *you* might have reached the same conclusion as I did: the only way for me to live, is as a woman.

 

* * *

 

I took a 3 month leave of absence from work, and flew to Denmark, where there was a clinic that would take me. It was a whirlwind of activity once I reached there. Electrolysis. Hormones. Breast implants. Facial surgeries. Hip implants. Liposuction. And of course, the main event, *the* operation.

And then, as with any major reconstructive surgery, my body was bruised, I hurt, and I looked like I had been in a car wreck. It took a long time to heel, and I just barely made it back before the 3 month leave of absence was over. But every day, I wrote to Tawny, and once a week she wrote back.

 

I had made arrangements with my company to change my employment status from male to female, from Craig to Karen, and all that it entailed. I had to do a legal name change, get a new drivers license, do the paperwork to get the government to classify me as female, and all the other million little details.

I showed up for my first day of work as a girl, and I felt like every person in the place was staring at me. I wasn't pretty like Tawny or Veronica. I still had some manly traits. But I looked and felt womanly, as much as modern medicine could manage transform me.

I went to Veronica's desk first to say hello, and she was very kind and supportive. She told me I looked very pretty, and that I made a great woman. Then I went to see Tawny, now that my courage was up.

But she wasn't at her desk! I went back to Veronica's, to see where she might be. I would have expected her to be there on my big day.

 

"Oh, she's on her honeymoon" said Veronica. "Didn't you know that?"

"Honeymoon?" I said, absolutely floored. "What do you mean? She was in love with me, remember? That's why I did all this!"

"Oh silly" said Veronica. "She was engaged all this time to Roger, you know. He just got out of the army, and so now she doesn't have to save herself for him anymore. Didn't you notice his picture on her desk?"

"But we made love together!" I said.

"Yes. They had an agreement. She could have women lovers, but no men. She is 'bi', and likes both. Roger thinks having 3-ways with a chick is hot, so he encourages her to see other women too."

"But you told me that if we were to be together, I had to do all this!" I said, now on the verge of tears. My life was ruined, and everything I had worked for was crumbling around me.

"It's only fair" she said.

"What do you mean?" I asked, not understanding her point.

"Well, lets see. You made me think you were interested in me. You made me fall in love with you. Then you broke my heart, because you were just using me to get to Tawny."

She knew! How did she know? I had been so careful in my planning!

"And so, now I've done the same thing to you. You made me into a brokenhearted woman, finding that her potential love had been snatched away. And now, *you* know how it feels to be a brokenhearted woman too."

"No!" I cried. "This can't be true!!!!"
"It is" she said. "You never wondered why I was so eager to turn you into a girl? You never wondered why Tawny would never pay you any attention as a man? You just failed to see what was happening around you. And now you're in the same boat that I was."

I broke down and cried. Veronica had started to turn me into a woman, but I had done the last part to myself. Now I was stuck, unable to ever go back to who I was. I had become a woman to win Tawny, but she was gone forever, married to another man.

Well, not 'another' man, because I wasn't a man anymore, at all.

"Don't cry, dear" said Veronica in mock sympathy. "There are lots of men out there who would love to date you. I'll work on finding a nice man for you, and you can fall in love with him. I'm sure the guys will love your nice hard big boobs. You'll put out for them, won't you? You want a man now. I can tell. I can see it in your eyes."

"I just want Tawny" I sniveled.

"That's just not going to happen. Now you had better dry off your eyes, fix your makeup, and get to work. Just because you're a girl doesn't mean that you can go around gossiping all day with me. You have work to do. What would your boss say? You're all emotional now that you're female I see, but that is something you'll adjust to. See you at lunch, girlfriend."

 

She walked away, and I stood there stunned. I was a woman now, without a girlfriend, and knowing that I'd never love a man. Unless I could find a woman like Tawny, who liked other women, I would always be alone. But how could I ever love again? To say I was crushed was an understatement.

With my head down, I walked slowly to my desk. The imprisonment of my new life had begun. Veronica was right. I had done this all to myself. It was all my fault. I was a girl now, and there was nobody to blame but me.

I had done this all to win her over. And in the end, all I won was a new female body, and a new life as a woman. Maybe Veronica was right. Maybe some day I'd fall in love with a man. But for now, all I could see were dark clouds. I took off my high heel shoes, turned on my computer, and went to work. What else could I do?

  

  

  

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