Crystal's StorySite


The Organization

by Carlito Esperanza


Chapter 1

The Interview


I was looking for work. With a good bit of experience in IT, accounting and fund raising, you would think it wouldn't be too hard to find something. But I hadn't had much luck. Then on about my fourth trip to the private employment agency, the lady laid one on me. She said, "I have a job that matches your qualifications almost like it was made for you. And the salary is in the range you had mentioned. But there is one detail you should be aware of."

I hate it when they say, "But. . ." It is always a preface to some nasty little detail that negates everything that has gone before.

In this case she said, "The organization is a women's group. Some would call it feminist. If they hire you, you probably would be the only man working in the office. The organization can't say it out loud because of the equal employment laws, but they would really rather have a woman. The trouble has been finding a woman with the qualifications they need. I've shown the job to some other men and they immediately cut and ran. Do you want to look at it?"

I mulled that over for a while and then said, "I'm not into this war of the sexes thing. Will I have to file a sexual harassment suit in six months?"

"No, I don't think so. They are not that much into the war of the sexes either. But you will undoubtedly hear some comments at least at first. However, I talked to manager before I showed this job to any men and she assured me that if you do your job and don't make an issue of sex, they will even be nice to you." She grinned.

"OK, I'm game. I'll at least go interview for the job. They surely won't attack me at first sight."

She laughed. Then she made a quick call and when she hung up, handed me the paper with the contact information and a time on it and wished me well in the interview. You know she was sincere because she would get half my first two months pay if they hired me.

I arrived at the address 5 minutes before the appointed time dressed in suit and tie. The building was a single story brick on the edge of the downtown area with visitor parking in the front and a sign indicating employee parking in the rear. I parked in the front and entered. A nicely dressed middle aged woman at the receptionist desk gave me a frosty smile and said, "May I help you?"

"I have a 2 o'clock appointment to see Ms Brown," I said.

"Have a seat over there, please. She will be with you in just a minute."

I had hardly sat down when a woman appeared at the corridor opening and called me by name. I rose and she motioned me to follow her. We walked past several offices where women were working. We turned into the last office and she pushed the door mostly closed. Ellen Brown was in her mid thirties I guessed, medium height, blond and well dressed in a dusty rose suit with matching blouse. She motioned me to sit then she took a chair opposite me but not behind the executive desk. When she sat, she crossed her legs and let her skirt ride up enough to show a lot of leg. I forced my eyes to stay on her face and not look down at her legs. But out of my peripheral vision, I could tell I was being tempted with quiet a show. After a little she tugged at her skirt and covered her legs. I began to breath again.

"As you are aware we have had some trouble filling this position. Finding the right person has been difficult. Therefore we are offering a salary on the high end of the market range. I'm sure you are aware our organization is composed entirely of women and working here will be a test of your diplomatic skills."

"Well, I have worked with women before and we got along fine. I don't have anything to prove."

"How do you feel about having a woman as your supervisor?"

"I've never had that experience. But I think that as long as we understand each other and communicate what we expect, it shouldn't be a problem."

"Oh, one more thing. As you probably have already noticed, everyone here wears dress clothes. 'Casual Friday' here means slacks instead of a skirt. That means that you will be expected to wear a coat and tie every day. In the office you may take your coat off but the tie should remain in place. Any problem there?"

"It will take a little getting used to but I can handle that."

She rose from the chair, extended her hand and said, "Welcome aboard, Carl. And here in the office you may call me Ellen. Report to me at 8 am tomorrow. You may park in the number 11 space behind the building and come in through the back door."


Chapter 2

The First Day


I reported to Ms Brown at 8 o'clock and was shown to a vacant office. That

would sure be better than the cubicles we had at the last place I had worked.

More space, less noise and some privacy if need be.

I spent the first couple of hours discovering what was on my computer and in the drawers of my desk. The previous occupant of the office hadn't done a very thorough job of cleaning out. There were lip stick tubes and mascara and a compact in the drawer along with a couple of tampons. The "My Documents" folder on the computer was full of personal stuff, too. I made a mental note to delete the personal stuff once I was sure what was personal and what wasn't. I began to suspect that the previous occupant had been dismissed and left in a hurry. I picked up the organization personnel manual and reread my job description. Then I began to explore the computer program that would be the main stay of my job. It wasn't very different from the one I was familiar with, just a huge data base with a front end designed to facilitate fund raising. The only thing to learn would be the vocabulary of the organization.

About 10 o'clock a voice came over the telephone intercom, "Break time, Carl. Come on to the break room at the back of the building and meet the rest of the staff." Should I wear my coat or not? I debated for a moment and then decided that since this was break time, I wouldn't.

In the break room I was introduced to the others: Renee, Liz, Barbara, Alice, Jane, Martha, Dot, Nancy, and Sandra. Suddenly, I knew how a girl must feel when a bunch of guys are checking her out. I could tell they were really sizing me up and deciding if I could stay. I smiled and acknowledged each introduction. Then I poured a cup of coffee and sat down. After that I was ignored and the conversation went on as if I were not there. When break was over I returned to my office.

Ellen stopped by and apologized for the others. She said, "They aren't used to having a man around here and don't really know what to do with you yet. But they will loosen up in a day or so." That was some comfort. It wouldn't be easy to stay if I were always ignored like that. And over the next few days they did loosen up. I was careful to not stare at anyone who was a little careless in crossing their legs and showing too much, or leaning over and giving too good a view down their dress. I was careful to be nice and not say or do anything that would give anyone a reason to not like me.


Chapter 3

Plans For The Convention


Over a period of weeks I became like "just one of the girls." We talked about work, diets, family, clothes and occasionally about men. When the subject got to men, I just kept quiet. I didn't try to deny the accusations or defend the actions they complained about. That would have been bad politics. Once in a while someone would make some nasty remark about men in general and then add,

"Present company excepted" and grin at me.

When I had been there several months they began to talk about going to the national convention. About the second or third time the subject came up, Renee asked me, "You're going aren't you, Carl?"

"Well, I hadn't really planned to. I don't think I would fit in very well there if you know what I mean." There was a round of laughs.

Then Ellen said with a very serious tone, "But you really must go. You need to meet people from other offices and give a report about the excellent job you are doing with fund raising. And if you don't feel at ease going in a suit, you can go in a dress. We will help you."

I must have blushed beet red. "You're kidding aren't you?" I stammered.

But Liz chimed in and said, "Don't worry about it. The convention is over a month away and by that time we will have you properly dressed and comfortable as a woman."

After coffee break I went to Ellen's office and asked her about the conversation. "We were quiet serious about it. We will all work together to get you ready so that you can go to the convention and feel at ease."

"But . . ."

"OK, it is time to lay it out for you. We had looked you over really closely before you were even shown the job at the employment agency. We know that you are a 'closet transvestite'. And we like you well enough that we want to help you to be able to go to the convention and enjoy it. Dressing up and going out with the girls is part of the experience. And we do want to you to give a good report at the convention. Your work speaks well for this office."

My jaw must have dropped into my lap. "I didn't think anyone knew about my little hobby."

"I know it wasn't legal and probably not even very nice to do that to you. But we had to be picky about who we hired. Not just any man could or would work with us like you have and we hadn't been able to find a woman to do the job. You have been a good member of the team and I suspect that it is because you of as you say, 'your little hobby.' Your feeling about women is in sympathy with them.

"Now, as to how we will help you, this is what we will do. This weekend Liz and Sandra will work with you on clothes and makeup. The organization will cover some basic 'start up' costs and there is a raise planned for your next pay check. Then beginning Monday you will come to work in a dress. No one will make any comments about your appearance or change in dress. Renee did some drama in college. She will coach you in body movements and voice. Your work load is not too heavy right now and you can spare the time to work on all this here in the office. I think everyone will also be glad to help you outside the office.

"There is some risk in going outside but I will arrange a 'valid' driver's license for you so that if you should be stopped, there would be no problem with the police.

"Of course you can insist in not participating in our little plan. I won't fire you for that. But I believe that you will enjoy going along."

Was that a not too thinly veiled threat? I was being blackmailed and I didn't know if I liked it or not. The idea of having serious help with clothes and makeup appealed to me. The prospect of having to live as a woman for more than a month terrified me. And I knew that although Ellen had said that she wouldn't fire me if I refused, she could wait until my annual performance review and give me such a bad report that no one would believe me if I complained. Besides, I liked the job and the atmosphere that I worked in.

I thought about it for a very brief time and agreed. "When do we start?"


Chapter 4



"Why don't you go talk to Liz? She will tell you what to do."

I left Ellen's office and walked across to Liz's. She smiled and indicated a chair. In a minute she finished what she was doing and turned to me with a smile.

"Ellen convinced me and said that I should talk to you about when to start."

"How about tonight? Can you give us the whole weekend? Come over to my place and have dinner with Sandra and me. Bring you stuff so that we can see what you have and make a list of what you need. Then, in the morning we can go shopping if necessary. Will that be a problem?"

"Oh, I can handle eating someone else's cooking anytime. And I haven't got

much "stuff" so it won't be hard to bring it all. Do you think anyone will notice a man going into your place with a suitcase?"

"Don't worry about being seen. Just come on like you belong there. I'll see you about 5:30 but dinner will be a little later than that."

After work I went home and carefully packed my 3 dresses, some panties, the two bras and the one pair of shoes I owned into a small suitcase. I added the one full slip and one half slip, two pair of pantyhose, one black and one neutral and the wig. Then I gathered up the little bit of makeup I owned and put that in a plastic bag and tossed it in. The few pieces of jewelry followed in another plastic bag. As I looked at the still half empty suitcase I thought how pitifully poor my wardrobe was compared to that of the women I worked with. They all dressed nicely in a variety of clothes. It was not without some misgivings that I put the suitcase in my car and headed off to Liz's place.

She lived in an upstairs apartment in a nicer than average complex. When I arrived at her door, it was ajar and I heard her say, "Come on in." She must have seen me arrive in the parking lot.

She took the suitcase and put it in a bedroom. "Sandra will be here in a few minutes. Would you like something to drink while we wait? I have diet cola, orange juice or milk."

"Thanks, I think I had better have just water."

As I sipped on the glass of water I said, "I gather that I have been a little out of the loop. Everyone seems to be prepared for this except me."

"Well, I have to confess, we had discussed the whole project pretty thoroughly before we even started to talk about the convention in your presence."

"Oooh, sneaky!"

"Not maliciously so. Just thinking ahead."

Just then Sandra arrived. Liz greeted her with a light hug and a peck on the cheek and took the bowl of whatever it was from her and carried it to the kitchen. When she returned she said, "All right, you two go do your thing while I put dinner on the table."

I stood and Sandra led the way into the bedroom where Liz had placed the suitcase. "Tonight we will just see what you have and how it looks. Go ahead and open the suitcase."

I placed the suitcase on the dresser stool and opened it. I put the shoes on the floor and spread the rest of the contents on the bed. Sandra glanced at the shoes, sandals with 3 inch heels, and then moved on to examine the clothes on the bed.

Then she turned to me and said, "There is depilatory cream in the bathroom. Do you know how to use it?" When I shook my head negatively, she said, "Rub it all over your legs, chest, stomach and your back as much as you can reach. Wait 20 minutes and wash it off in the shower. Then use some of the body lotion that is there. It will sooth the sting. When you finish, put these on and come back." With that, she tossed me a pair of panties. "Oh, and shave your face and armpits too. You don't look like you need a shave but just to be sure."

When I returned half an hour later she held up one of my dresses and said, "This looks like a nice dress. Where did you get it?"

"At an unclaimed baggage store. Why? What's wrong with it?"

"Hey, I like that! You reacted like a woman. Taking the question about where you got it as criticism. That's a woman thing. Why don't you wear it to dinner? When you are dressed, call me and let's see about your makeup." Then she stepped out of the bedroom pulling the door closed behind her.

The dress was my favorite, a little black dress with tiny pleats all around from the jewel neckline and shoulder seams to the bottom which had no hem. It had elastic at the waist. On the hanger it hung straight and shapeless. But on, it accented every curve beautifully, not that I had many curves except what the padded bra provided. And accessorized with pearls, it made a fabulous dress. I picked up a black bra and put it on. I filled the cups with the falsies I had and sat at the dressing table to pull on the black pantyhose. There was certainly a different, more sensual feel to the hose on my now hairless legs. Next I pulled the black full slip over my head and smoothed it down over my body. I really liked the feel of the slip against my skin. I put on the shoes and fastened the straps. Finally, I pulled the dress over my head and smoothed it down my body. From the bag of jewelry I took a string faux pearls and fastened them around my neck. I found matching ear clips and put them on. Finally, I put on the wig and gave it a quick combing. Then I turned and looked in the mirror. From the neck down, not bad. Not bad at all. But my face still looked like me, a man.

I opened the door and called Sandra. As she entered the bedroom I did a slow turn to so that she could get the whole picture.

Sandra looked me up and down carefully and then nodded her head in approval. "You do right well with the clothes. Now, let's see about the makeup."

I sat at the dressing table and spread out my very small stock. Sandra looked at each item critically and then said, "You might want to take the wig off." I did. Then she said, "Go ahead and do what you usually do. That way we will know what we are dealing with."

I applied a little blush, some mascara and lipstick. "That is really all I know how to do. I've never had anyone to teach me and never felt brave enough to buy some things and experiment with them."

"Very well, your face looks much too casual for the dress. But better too little than to look like a clown, which is a common problem with people who don't know how to use makeup correctly. Put the wig back on and we'll be ready for dinner."

Just then Liz called, "Dinner is ready. Come on, let's eat and then we will plan our shopping trip for tomorrow."

As we ate I did my best to be dainty and eat like a woman. I watched Liz and Sandra and tried to do things like they did, pulling food off my fork with my teeth and my lips open so as not to spoil my lipstick. I blotted my mouth with the napkin instead of rubbing it as I normally would. The hardest thing was sitting stiff backed on the first six inches of my chair instead of slouching. I remembered what Mrs. Smith, my piano teacher had said to me many times, "Sit straight, shoulders square." Of course, she was talking about sitting at the piano. But the lesson applied here, too.

The meal was light. A congealed salad, a very small piece of broiled chicken, some raw carrots and grapes for dessert. It was hardly half what I probably would normally eat. As we cleared the table, Liz asked what I thought about the meal.

I replied, "It was fine, what there was of it."

She grinned and said, "Get used to it. That's part of the discipline of being a woman. Your 'super size it' days are over."


Chapter 5

The First Shopping Trip


After dinner we sat in the living room while Liz and Sandra discussed my needs. But their first question surprised me. Liz asked, "What's your credit card situation? Can you spend a couple of thousand without busting the limit?"

I must have paled visibly. I had a gold card that would easily cover that much because I was very careful about my purchases. I had no desire to go into debt for this little experiment.

"Oh, don't get up tight about it," chuckled Sandra as she watched my expression. "The organization will buy you one outfit and we will make sure that it will be mix and match so that you can get as much use from it as from three. The expensive things will be a good wig, breast forms and a first class make-over so that you will have the right shades of makeup and know how to use them. But all of those things are really long term investments."

Still, the list of things they planned to buy seemed long and I was sure that I would be close to the limit on the card if I had to pay for it all.

We agreed that I wasn't ready to go out in public in a dress so I would go shopping in male clothes. They had me strip down to my bra and panties and then took several measurements to prepare for buying clothes without my being able to try them on.

"Liz, where is the cleansing cream? He doesn't have much makeup but he needs to learn, beginning now, to take it all off every night and moisturize his skin."

As I prepared to leave, Liz said, "Leave your stuff here. And beginning tomorrow you will move in here with me for a couple of weeks until you get the hang of things." It was obvious that I had lost control of my life.

The next morning I dressed casually, had a light breakfast and met Sandra and Liz at one of the larger malls in the area. Sandra was already carrying a bag as if she had made a purchase.

Our first stop was a shop that specialized in "foundation" garments. Liz explained, "These are called foundation garments because a good shape is the foundation of well fitting and nice looking clothes. Even expensive clothes don't look good over a poor foundation."

We walked in and Sandra immediately said to one of the women whom she apparently knew, "Silvia, this is the person we told you about." The woman smiled at me and motioned us toward the back of the store. There were four large fitting rooms. Each had a full door so that not even feet or head could be seen from the hall nor could conversation be heard. And the room was only a little crowded with four of us in it.

The woman said, "Take off your clothes." Neither she nor Sandra or Liz offered to leave. I wasn't very comfortable with the idea but what could I do?

I stripped down to my panties. The three women smiled when they saw the panties. Then Silvia took a tape and measured me again, a couple of places around my chest, my waist, my hips and my thighs. Then she picked up a large ring with lots of little squares of different colors. She turned me so that there was good light on my chest and began to hold first one then another of the cards against me. At one point, Liz said, "That looks pretty close."

After a couple more checks, Liz face brightened and she said, "That looks perfect to me."

"Yes, I think that is a good match" agreed Silvia. She looked on the back of the card and noted the numbers. Then she left the room.

When she returned in a few minutes Silvia was carrying two boxes and several items of clothing over her arms. She placed everything on the small table and picked up the first piece, panties. "Here, put this on."

As I pulled the panties on I realized that it had padding on the sides and in the back.

Silvia opened one of the boxes and took out a breast form. "These can be glued on if you like. But for short term wear, you put them in the pockets of these special bras." With that, she worked the form into the pocket of the bra cup. Then she picked up the second form and put in the other side of the bra. "Put this on" she ordered. Putting the bra on was different because of the weight in the cups as well as the bulk. When I pulled the straps on to my shoulders I felt the weight of the forms Silvia reached up and adjusted the straps and tugged at the band of the bra to get it properly fitted to my body.

At this point Sandra opened her sack and pulled out a black full slip and handed it to me. I pulled it over my head. Again, Silvia adjusted the straps to make it fit my new shape better. Then Sandra handed me the little black dress I had worn the night before. I pulled it over my head and smoothed it down my body. When I looked in the mirror I realized what Liz had meant about foundation garments making a difference in the way clothes look. I had more feminine hips, butt and breasts. The dress really looked much nicer than it had before.

As I started to undress, Silvia stopped me and measured me over the bra and panties. She noted the numbers and handed the paper to Sandra who looked at them and smiled. "This is going to work out just right. Just as I thought, your measurements are very close to mine. That means that as we shop for dresses, I can try them on and we will know pretty well how they will fit you."

We bought the breast forms and two bras to hold them. We also took two padded panties. And my credit card took a real hit. $300 just for the breast forms plus another $200 for the bras and panties. It would take a good while to amortize this investment.

As we left the shop Sandra handed me a sack with the breast forms and said, "I'll put the rest of this stuff in the car and meet you in the lingerie store." There would be other trips to the car that day.

As we walked toward the lingerie store Liz explained that appropriate lingerie makes clothes fit well and nice lingerie makes even a plain girl feel more elegant. I could tell that my credit card was about to take another hit.

Although I had been in the lingerie department of some stores I had never felt free to linger or to handle the merchandise. Now Liz began to pick up hanger after hanger of panties and hold them out toward me and ask, "What do you think about this style? How do you like this color?" At first I was embarrassed and blushed but after a bit I realized that no one was paying any attention to us. We selected several pairs of panties and then moved on to bras.

"Since you have the breast forms you don't need padded bras but we will have to try on our choices to see that they fit right." I wasn't too keen on that but after we had chosen several, Liz laid the panties on the counter by the cash register and told the girl, "We are going to try on bras."

We walked into the fitting room, this one with only a curtain, and she told me to take off my shirt. As I tried the various bras I understood why Liz had said to try them on. Although they were all marked the same size, 36 B, there were differences in the fit. One was too large in the cups. Two others were too tight around my body. In the end we chose three smooth cup models that would go well under sweaters Liz said, two with wide set straps and lower cut cups, "so you can show off your cleavage," and a couple of lace covered ones, "that will look nice under semi-transparent blouses." Sandra joined us while I was trying on bras and approved our choices.

I put my shirt back on. As we headed toward the check-out counter we picked up a waltz length pink gown with a flimsy matching robe and a pair of baby-doll pajamas. Then we returned to the check out counter and I paid for our purchases. The girl at the cash register looked at me kind of funny as she put our purchases in a bag but she smiled and said, "have a nice day."

Liz directed us toward a ladies shoe store. You really need some better fitting shoes, and a variety, too. We studied the shoes in the window and discussed what types I needed. When we had settled on basic styles and agreed that we would buy three pair of black shoes we went inside. Sandra commented that later I would want to buy other colors to coordinate with my outfits. Liz produced a pair of ankle length hose from her purse. "Here, put these trouser socks on so that you can try on the shoes."

We asked the salesman for the three styles we had agreed on. He brought out the shoes in the size indicated and looked first at Sandra and then at Liz to see which would try them on. I cleared my throat and said, "They are for me." He rolled his eyes but opened the first box and slipped a pair of pumps with 3 inch heels on my feet. "These are a bit tight. I think a half size larger would be better." He took all the shoes back and returned with the larger size. This time the pumps fit. I walked around some to confirm that they felt right then I tried on the sandals which had 4

inch heels. The third pair had very low heels and fit well. "Oh, I almost forgot, we need some house shoes, too" said Liz. I picked a pair of slides with two and a half inch wedge heels in a shade of pink that matched the gown we had bought. I paid for the shoes and as we left the store Liz took the bag and said, "This time I will go to the car. Meet you in the misses department of Belk's."

We spent a good bit of time looking through the racks of dresses. Sandra would pull one out and hold it up. "What do you think about this one?" If I didn't react strongly in favor, she put it back. I tried not to look at the prices. I was already in too deep to worry about that any more. Sandra held up a filmy looking black dress that she said was a Georgette print. It had a crossover ruffled hem and flutter sleeves and a V-neckline. "Isn't that just darling," she asked? I almost drooled as she laid it aside to try on. Next she picked a blue jacket dress. The dress was sleeveless and long. It came to her ankles when she held it against her body. The jacket came to mid-hips and looked fitted at the waist with flair at the hips. I smiled and she laid that aside to try on. The next dress that I liked was light colored with blue flowers and light green leaves.

We moved on to racks of tops. By this time Liz had joined us. She suggested some light weight short sleeved sweaters in colors that would work well with skirts we were to choose in a few minutes. Along with the others we picked up what Liz called a "twinset", a light weight sleeveless sweater with a square neck and a matching long sleeved V-necked cardigan.

"You will need to come back later and get a really dressy dress or maybe two. We really dress up for nights at the convention."

I noticed that both Sandra and Liz were working the sale racks first. And I was glad for that. After we had chosen half a dozen dresses Sandra took them to the dressing room and modeled each for us. We chose another 3 skirts and blouses which Sandra also tried on. Then Liz led the way to the more expensive clothes. After a lot more looking, we finally chose on a blue mix and match set that included jacket, skirt, dress and pants. I already had a blouse that would work with the skirt, pants and jacket.

I whispered to Liz, "I'm not sure that buying pants is a good idea. I'm afraid I will have an unladylike bulge in them."

She grinned and said, "We have thought about that and we will take care of it tomorrow."

I paid for the skirts, blouses and dresses. Liz produced a credit card

with the organization name on it and paid for the mix and match set. And I was

certainly glad that she did. To a girl who had done all her shopping at unclaimed baggage and thrift stores, we had just spent an astonishing amount of money.

"Let's break for lunch then just two more stops and then we will call it a day," said Sandra.

While we ate Liz ask if I had a fem name. "I've used Carol because it is so close to Carl. But I think I would like to try something different." We played around with names a bit and finally I said, "Cheryl sounds good to me."

"All right, Cheryl it is then."

"We still need to get you a better wig and the right shade of makeup."

The wig store in the mall didn't offer anything that looked to be of the quality that Liz and Sandra were wanting so we consulted a phone book and left for a store across town that promised more.

Once there, Liz explained to the lady who attended us what we needed. She took me to fitting room so that we would have some privacy. Then she measured my head. We discussed style and color. The color decision really wasn't difficult. My hair is sandy blond so we decided to stay with that color. After looking at several, we settled on one with loose curls that came to my shoulders. Contemporary but the lady assured us that it would be low maintenance. I put it on the card. Ouch!

From the wig store we went to a shop in a strip mall. Sandra greeted the lady and said, "Donna, this is Cheryl. I mentioned her to you. She needs some help with choosing the right colors."

Donna didn't bat an eye. She just set me in front of a mirror with lights all around. Then she began to change the color of the lights, more orange for evening she said, then more blue for daylight. All the while she was studying my face. Finally, she returned the lights to a more neutral setting and walked away. In a few minutes she was back with several bottles and tubes. "First we need to thin those eyebrows a bit," she said. She picked up tweezers and began to pluck. When she was through, my brows were decidedly feminine in appearance. She applied something from a tube to hide a couple of blemishes and a small scare. Then she began to work a liquid all over my face and neck. When she finished that she used powder of the same shade to "set" the foundation. Blush accented my cheeks bones and a touch of a darker shade than the foundation appeared to make my cheeks thinner. She put two shades of blue eye shadow above my eyes and used a pencil to outline my eyes. Then she applied mascara to my eyelashes. Finally she outlined my lips with a brush and then applied lipstick.

As she was finishing, Liz went to the car and returned with the wig. Donna seated it on my head and then turned me to the mirror again. I had watched the whole process but I had been so interested in the details that I hadn't seen the whole. Now, I saw my whole face framed by the loosely flowing curls. I could hardly believe what I saw. Not a beauty queen, but at least as pretty as average feminine face.

I paid the bill and left with a sack full of cosmetics, still wearing the wig and makeup.

It was dinner time when we arrived at Liz's apartment. The meal was similar to the previous night. After dinner we began trying on the clothes. Of course that meant putting on the padded panties and the bra with the breast forms. By this time Liz and Sandra had seen me in all stages of dress and undress enough that they didn't offer to leave the room while I changed and I didn't feel too embarrassed with their presence.

The blouses and sweaters seemed tight around the shoulders and arms but Liz and Sandra said they fit fine. The fuller skirts were also OK. They had elastic around the waist. But when I put on the straight skirts Liz groaned and said, "Yes, we definitely are going to have to deal with that bulge tomorrow."

The pants got the same reaction but otherwise the "mix and match" outfit was a good fit. Three of the dresses would have to be returned. They just didn't fit right. Although our measurements were essentially the same - height 5 feet 6 inches, bust 36, waist 26 and hips 35 (her waist an inch smaller) -- even with the help of the foundation garments Sandra's body and mine were not exactly the same shape. We were all surprised that we had done as well as we had in purchasing clothes without me trying them on.

As I was putting on one of the outfits Liz said to Sandra, "You know what we forgot? We didn't buy any jewelry. No ear rings, bracelets, necklaces, no watch."

By the time we had finished trying all the clothes I was exhausted. Sandra sensed my desire to go to bed. She gave me a hug and a kiss on the cheek, said her good bye's and was gone. Liz handed me the cleansing cream and the moisturizer and I started to clean my face. I discovered that was to become as much a nightly ritual as taking off my clothes and putting on a gown.


Chapter 6

The Second Shopping Trip


When I awoke I was disoriented. The room was strange. The feel of the gown was strange. I wondered if I was dreaming all that had happened. Then I remembered, I was in Liz's guest bedroom. I could smell coffee so I pulled the flimsy robe over my gown and went to the kitchen.

"Well, I'm glad to see that you survived yesterday," grinned Liz as she poured me a cup.

"Oh, yes, I survived and I have to confess, I enjoyed the day except that it was tiring."

"We probably will not do another big shopping day like that. It was a bit much even for me."

I sipped my coffee and asked, "What is the program for today? You mentioned that there were still things to do."

"There is still a little shopping to be done. We need to get you some jewelry and a gaff."

"Where will we get a gaff? And by the way, how do you know about things like that?"

"I have been studying up on crossdressers and transvestites since soon after you came to work with us."

"So everyone has known all about me from the beginning?"

"No, not everyone. Ellen brought me in because she knew that if we ever got to this stage I would have to be the leader. She and I evaluated your attitude and your habits and made the decision to take you to the convention. Then we told the others one at a time. We took it slow and easy so that they had time to get used to the idea and so that anyone who wasn't cool about it wouldn't upset the deal. Fortunately, everyone accepted the idea pretty well."

Liz set out several boxes of cereal and a gallon of milk. "Let's have breakfast and get dressed. Then we will get the gaff and after lunch we will pick up Sandra to help choose the jewelry."

"What should I wear?"

"One of the more comfortable skirts and blouses and carry along that tan straight skirt. It is the tightest one, isn't it? We will have to go to the big city to make this purchase. I made us an appointment for 11:30 and it will take about two and a half hours to get there so we had better get moving."

After my shower and shave I put on beige panties, one of the padded panties, the bra with the breast forms, nude pantyhose and a beige half slip. Then I chose a white nylon blouse with a large square collar and a red crape like skirt that came to below mid calf. I slipped on the new sandals and sat down to do my makeup. I tried as best I could to do exactly what Donna had done the day before. But after several minutes I opened the bedroom door and gave a plaintive cry, "Liz, can you help me. I can't get my makeup to look right."

Liz came and looked at me with a twinkle in her eyes. Then she gave me a hug and said, "You did very well for a first time but let's clean it off and I'll coach you and help." Twenty minutes later I looked much better. Then I set the wig on my head and walked to the mirror. Turning slowly, I admired myself. I had never looked so good. At Liz's suggestion I picked up a purse with a long strap, put my wallet, lipstick and a small pack of tissues in. She watched me and then said, "Wait just a minute." She went to the bathroom, returned with a tampon and dropped it into the purse. "That's a seal of authenticity of your femininity," she grinned. I slung the purse over my shoulder and we headed to the car.

On the trip down the stairs and across the parking lot to the car I was very nervous. "What if someone sees me?" I asked.

"Then they will think that I have a good looking young woman visiting me," responded Liz with a smile.

As we drove to the city Liz asked me how I got started wearing women's clothes.

"I don't really remember when I started or what got me started. But by the time I was ten or eleven I was experimenting with my older sister's clothes. She caught me but instead of making a big fuss she helped me a few times. Soon she stopped but I didn't. I dressed from the dirty clothes hamper or when I thought I could without getting caught, I would slip into her room and try her things. I don't think my mother every knew."

"Oh she knew, all right. Mothers have a way of knowing all kinds of things."

"You've talked to my mother?"

"Ellen told you that we checked you out thoroughly before your were hired.

And we kept checking as we got to like you more. "

"As you got to like me?"

"Yes, we saw that you could do the work and that you fit well with our team and we wanted to know how far we dared go with you. You are not homosexual are you?"

"No, I don't have a girlfriend at the moment, but I definitely am not interested in boys. I guess I must confess that I really have very limited sexual experience."

"That is sort of what I thought."

We turned off the interstate and worked our way into a part of the city that I wasn't familiar with. It looked a little seedy to me. Finally we stopped in front of a store with a sign that said, "Being You - Clothes for Men and Women."

Liz checked her watch and said, "Good, we are right on time." We walked to the door. It was locked. Liz rapped on the glass. In just a minute a woman answered the door and let us in. Then she locked the door behind us.

"I'm not usually open at this hour," she groused.

"I'm sorry for the bother but we have come from out of town and have to get back early. This was the best we could do."

"OK. But you should have brought your boy friend with you. We can't fit a gaff properly without him."

Liz laughed and pointing to me said, "This is him."


The woman, whom Liz called Sue, showed us several articles of clothing that looked pretty much like panties except they were of heavier material. We chose two beige ones. Then Sue showed me to a dressing room and said, "Try these on."

I had read about a gaff and knew basically what it is supposed to do and how to make it work but putting it on was a whole different experience. After considerable pushing and pulling I managed to get the gaff in place and present a smooth front. Then I put back on the padded panties and the straight skirt and walked out of the dressing room to show Liz. She looked at me carefully and then indicated for me to turn sideways so that she could see the profile. "Yes, that looks good. How does it feel?"

"Tight but I think I can learn to live with it."

"OK, now try the other one. You can't just assume that it will fit the same."

The second gaff did not fit as well. Sue brought me another. It fit more like the first. So we bought the two.

"Boy, two hours travel each way just to make one little purchase."

"Yes, I know it seems ridiculous but we want you to look good in whatever you choose to wear."

After a light lunch we picked up Sandra and returned to the mall to shop for jewelry, this time with me en femme. The first stop was to get my ears pierced. Then we chose a variety of ear rings, some bracelets, a couple of necklaces, a woman's watch and some rings. By then I was beginning to worry about the limit on my credit card.

"I think we have you pretty well set up for now. Let's go home and rest some. We will have to get up early tomorrow to get you ready to go to work."

After we put away our purchases we returned to the living room and Liz turned on the TV. Then she put a tape in the VCR. It was "How to Walk Like a Lady." We sat on the couch and watched the tape. At two or three points I asked her to replay a section of the tape. Then I stood and tried to do as the tape had suggested.

After a while Liz asked, "Do you dance?"

"Not well. Why?"

"You need to learn. Let's dance. I will lead." She put on a CD with big band music from the '40s. We danced several numbers. At first I had trouble with the whole idea of moving backwards. But gradually I began to feel more at ease. And following her lead was easier than having to lead. And I liked being held close to her. On the last number I laid my head on her shoulder and relaxed into her arms. That was easy to do since she was about 3 inches taller. As the song finished, she turned my face up to hers and kissed me on the lips. It was a tender kiss and did not linger but it sent a tingle down my spine.

"We need to talk," she said. We sat in easy chairs facing each other.

"I know all about you. I guess it is time you knew a little about me. I was married once and had a son. He liked to wear girl's clothes. When my husband found out he accused me of perverting his son. It wasn't true. Nickie had been playing in my clothes for a long time before I confronted him and before Paul found out. When I found out what Nickie was doing, I explained to him that he was playing a dangerous game but he continued. Paul and I fought and he left us. Not too long after that a gang caught Nickie wearing a dress. They beat him to death. He was only 15 and I had begged him to not go out alone. But he thought he could pass." She began to cry. I knelt beside her chair and put my arm around her and tried to comfort her. After a bit she stopped crying and said, "That was 10 years ago. He would have been about your age now. I can't let something like that happen to you. That is why I will do whatever I can to make sure you are absolutely believable." She stood and I hugged her again. We both wiped tears from our eyes.

Then she put on a CD with contemporary music. We stood facing each other and I just tried to imitate her motions.

"Say, I just realized, we haven't done anything about your nails. Let me have a look." Liz examined my fingernails. "I'm not an artist but I can do a little." We moved to her dressing table and she began to work on my fingers. She shaped and buffed the nails and then applied base and two coats of red polish. "We will have to leave the professional job for another day," she said.

When my nails were dry she said, "Enough. Let's go to bed. Tomorrow will seem like a long day to you." We hugged and kissed each other on the cheek. Then I went to my room and put on the gown and prepared for bed by cleansing my face and moisturizing it.


Chapter 7

New Girl in the Office


Monday morning we got up early. I showered and then shaved, more from habit than necessity, because I always shaved on Monday morning. I slipped on a pair of white lace panties and went to the closet to choose my outfit for the day. I chose a bias cut gray skirt that flared at mid-thigh that would come to just above my knees and a pink sweater with a round neck. Because the skirt was so fitted at the hips and upper thighs, I removed my panties and pulled on the gaff and arranged my masculine parts as comfortably as I could. Then I replaced white panties. I decided that it was time to glue on the breast forms so I called Liz and asked her help. I lay on the bed as she glued them on and then applied makeup to cover the seam where they ended. After the glue set I put on one of the beige seamless bras. Liz helped me adjust the straps so that it properly supported my ersatz breasts. After I put on the padded panty I sat and put on neutral shade panty hose, then a white half slip. I pulled the skirt over my head, smoothed it down over the slip and fastened it in the back and ran the zipper up. Finally I put on the pink sweater and stepped into black pumps.

At the dressing table I began to apply makeup as I had been taught - concealer to hide the scar and blemishes, foundation to make my face color uniform, powder to set the foundation, blush, eye shadow in two shades of gray, eye liner and mascara. Finally, I outlined my lips with the brush as Donna had done and then filled in with lipstick. I worked slowly and carefully. It took nearly half an hour. When I finished I set the wig on my head and gave it a light combing. "Pretty good," I thought to myself. But I knew I would have to pass inspection by Liz.

I stepped into the hall and saw that Liz was already dressed and in the kitchen with breakfast made.

When I walked into the kitchen she looked me over carefully and smiled as she said, "You are a fast learner. You did that well. But you forgot your jewelry." Then she gave me a light hug and a kiss on the cheek, turned me back toward the bedroom and gave me a pat on the tush.

I replaced the studs in my ears with small diamond loops, put on my watch and a couple of bracelets and a necklace that matched the earrings.

"Now you are complete," smiled Liz when I returned to the kitchen.

As we left for work I slipped on a pink long sleeved sweater that matched the one I was wearing. Then I slung the purse over my shoulder and followed Liz to the car.

On the ride to the office we discussed how to handle my change in appearance. Liz pointed out that we were arriving early, probably the first to arrive. Sure enough, no one else was there. Liz let us in, turned off the burglar alarm and turned on lights. She suggested that I go to my office and close the door. After all the staff arrived she would get Ellen to call a staff meeting and I would be introduced there. "Oh, and by the way. You should use the ladies restroom beginning today. You are just one of the girls now so be sure to sit and check your makeup and hair before you leave." She winked at me and gave a wicked little grin.

I sat at my desk and did the usual first things - unlocked my desk, stowed my purse in a drawer, turned on my computer and looked over the work that needed to be done that day. About 10 minutes after the hour, Liz tapped on my door and opened it. "Come on, the staff is gathered and wondering where you are."

We walked to the break room where Liz signaled for me to wait just outside the door. She went in and said, "Let me introduce the newest member of our team. Come on in Cheryl."

I stepped into sight. There was an audible catching of breath. Then someone said, "Wow! You really look great."

Another said, "Go, girl. Go!"

I heard someone say, "Is that really him?"

Then a line formed as everyone came to give me a hug and a kiss on the cheek and say, "Welcome to the team."

Ellen said to Liz and Sandra, "You two did an excellent job."

Liz responded, "We had good raw material to work with. It was really relatively easy. We got full cooperation from Cheryl."

After things calmed down we returned to our desks and got about the day's business. In a few minutes Ellen came to my office with a camera in hand. She had me stand in front of a blank wall and look straight at the camera - document pictures, she said.

At break time all the chatter was about shopping for clothes and how we had managed to get clothes that fit so well. Liz and Sandra confessed that they had more than a little lucky in that. No one commented that I had more hips and butt than Carl or how that happened. I could see that one or two were really looking at my breasts trying to see if it was all padded bra. Liz picked up on that too and said, "No, no padded bra there. Cheryl, do you mind if she feels of you just to prove it?"

I grinned and shook my head. Then Barbara came over and placed her hand on my breast. She pushed and squeezed and watched as the shape of my breast changed in response to the pressure of her hand. Then she said, "They feel real. Hey, I can even feel her nipple there. How did you manage that?"

"Ah, the marvels of modern science," laughed Sandra. But she didn't offer any more explanation.

As we were leaving the break room Renee touched my arm and said, "Let's go to the conference room for some work."

I assumed that she meant the kind of help that Ellen had said she would give me. I followed her to the conference room. She shut the door and turned to me. "You look really good. But you do have a problem with certain gestures and your speech."

"First, when you are standing, put your feet close together. Men stand with their feet spread, 12 to 18 inches apart. Women stand with their feet very close together, seldom more than a few inches."

I looked down. Sure enough, my feet were about 12 inches apart. I moved them together. Renee smiled. "I feel like I could loose my balance and fall very easily."

"Well, you don't have as broad a base as before, but you will get used to it.

Now, walk the length of the room and back." I did as she commanded.

"Good. Toes pointed straight ahead, steps almost like you are walking a tight rope. And not too long a stride. You have practiced that before, haven't you?" I nodded.

Then she pulled out a chair and indicated for me to sit. She pulled out another and sat facing me. I crossed my legs and tugged at my skirt. "Very good. Now, tell me about yourself."

As I talked she was making notes. We must have spent half an hour working on making my voice lighter and more feminine. "Your voice is not really any deeper than many women. You just have to learn to sound more like a woman."

When Renee decided that we had done enough she stood and said, "OK, back to the salt mine."

I stood and instinctively scrambled to hold the door for her. She reached out and pushed the door closed. "That is a habit you have to break. You expect men to hold the door for you and you don't just automatically hold the door for other women. You may, but it should not be that reflex action like you just did." Then she smiled and gave me a hug and a peck on the cheek. "Remember, you're a girl now." She turned and opened the door for me and smiled.

I stopped at the restroom. Renee followed me in. She must have sensed that it made me nervous. "Get used to it," she said. "Women often go to the restroom in pairs." She waited while I did my business in a stall with the door closed and struggled with the gaff. When I came out smoothing my skirt she smiled and watched as I checked my lipstick.

At noon Sandra, Liz, Renee and I went to a restaurant nearby. I let them give their orders first and followed their lead. I ordered grilled chicken with vegetables instead of the 8 oz sirloin and baked potato that I would have preferred. Liz smiled and said, "That'a girl. Soon those skirts that are a bit tight at the waist will fit nicely." Sandra and Renee giggled. The coaching continued throughout the trip to and from the restaurant as well as during the meal. Mostly it was subtle so that people around us wouldn't notice. Before we left the restaurant we all went to the ladies room and redid our lipstick. I was nervous but I kept telling myself I belonged there and no one was going to scream and call the cops.

By the time we got back to the office my legs were killing me so I changed from my heels to the flats. I was glad that Liz had suggested that I carry them along. She knew I wasn't tough enough to take 9 hours in heels.

The rest of the day was pretty normal. On the way home that evening Liz asked me what I had learned that day. I talked about the things that Renee and I had worked on and how glad I was to change out of the heels by noon. Then she said, "But what did you learn about relationships?"

I had to think about that a bit. Finally I said, "Wearing a dress seemed to break down the last barrier between me and the others. Before they had accepted me but always kept me a little at a distance. Today, that distance was gone."

"And how do you plan to maintain that relationship?"

I thought some more and then said, "By being careful to always be a girl and not doing something that they would consider a 'man thing' that is offensive to them."

When we arrived at Liz's apartment, I went straight to the bedroom and undressed. Getting out of that gaff was a real relief. I slipped on a zip front house dress and stepped into my house shoes. After I hung up the skirt and sweaters I went to the kitchen to help with dinner.

After dinner we again watched the video about walking like a woman and I practiced more. When we had finished that, Liz said, "Let's dance."

She put on a CD of slow dance music and we started to dance. "I keep trying to back out of my shoes," I said.

"You will have to learn to be comfortable in anything you wear. Keep practicing.

You'll get the hang of it in a minute." And I did after several minutes.

As we danced I laid my head on Liz's shoulder and enjoyed the feeling of being held close by a woman. Liz must have felt the excitement in my body. At the end of one number she stepped back a little and ran her hand down the front of my dress. "There is still a man in there," she grinned. "You said you haven't had much experience. You need more."

She led me to her bedroom. Liz was a good teacher. She taught me how to satisfy a woman as a man and promised me that another night she would teach me to satisfy a woman as a woman. That night was quiet a lesson.

Tuesday was much like Monday. The usual work and more practice with Renee. About an hour before quitting time Sandra took me to get a driver's license with my new face and name. To do that, she gave me a driver's license from another state that already had my picture and name. I wondered how they arranged that. At the DPS office all I had to do was had them the "old" license and furnish a local address.

With license in hand, we went to get my nails done. After some discussion with the technician we settled on acrylic nails that were just about one eighth inch longer then my fingers. That isn't much when you look at a ruler but oh what a difference it made in the way I used my fingers. Typing, picking things up, applying makeup, everything had to change. But I really loved the shinny red finish and how feminine it made my hands look.

That night over dinner I said, "Liz, I confess I am enjoying this but I do have a problem."

"What's that, Babe?"

"My landlady keeps pretty close tabs on my coming and going. It isn't going to be easy to explain to her what I am doing wearing a dress."

"OK, I'll talk to Ellen about that and we will see about helping you get another apartment and moving you out of where you are."

To prepare for the move I picked up a pair of hip hugger jeans and a sweatshirt with a sorority logo on it. The jeans really tested the limits of the gaff. And it passed. No bulge in the wrong place.

Toward the end of the second week we found an apartment that I could afford and that Liz and Sandra agreed was in a neighborhood safe for a single woman. I had never thought much about safety but it obviously was a concern to them. Then we went in Sandra's car to get my stuff. We agreed that the landlady probably would recognize Carl's car. I rang the bell at my landlady's door. When she answered I said, "Mrs. Goldberg?"


"I'm Cheryl McArthur, Carl's sister. I've come to collect his things. He was in an accident while he was home last week and won't be able to work for a while."

"Oh, I'm so sorry to hear that. What happened?"

"I don't know exactly but he will be laid up for a couple of months and then have some time in rehab so we decided to move him back home for now. Please show me his apartment. I have his key."

Carl didn't have much stuff except a computer, a small television, some books and clothes. Even so, it took two trips in the car to get everything moved. Then we vacuumed the apartment and cleaned the bathroom.

Renee met us at the new apartment and helped unload the car. Sandra said, "Now that Renee is here to help you, I've got to run. I need to visit my mother. As we were putting things away, Renee asked, "How committed are you to living as a woman?"

"Looks like I'm pretty committed, doesn't it?"

"Yes, but if you are really committed, you won't need these clothes any more. If you're not sure, keep them until you are sure."

I decided to keep the clothes for a while. For one thing, I still would have to visit my mother and I wasn't sure that I wanted to do that as Cheryl just yet.

Renee started the washer and put in the dirty sheets and towels from the previous apartment. Then she found clean sheets and called, "Come help me make the bed. It is much easier to do with two people." Working together it only took a couple of minutes and the bed was made.

As we finished Renee gently pushed me backwards onto the bed and said, "Now let's see how good the bed is. I've been waiting for an opportunity like this for some time." With that, she kissed me with a deep passionate kiss as she began to unbutton my jeans.

Later that night I called my mother and told her that I was coming home for a visit on Saturday.

Sandra declared Friday night of the second week as my 'graduation.' She, Liz and Renee agreed that I was ready to return to my apartment and continue on my own. That called for a party. We agreed to go to a nice restaurant for dinner and dancing. Sandra made reservations at a supper club where all the staff could sit together. The food was good and the conversation was light with almost no mention of work. Then the band started to play. One after another we were invited to dance. I was glad for the dancing lessons with Liz.


Chapter 8

A Trip Home


On Saturday the alarm awoke me early. As I showered I debated with myself about how to dress. Should I go as Cheryl? Or was it wiser to go as Carl? Could I even go back to being Carl for a couple of days? Finally I decided. If Ellen had already talked to Mother and she already knew about my crossdressing, she probably also had an idea what was going on in my life. She might get a shock seeing me at first, but I felt that she would accept Cheryl. Then the question was, should I go casual in a straight jeans skirt and top or something more feminine?

Finally, I decided to go all out feminine. I put on black panties, the black padded panty, sheer black pantyhose and a black half slip. Then I put on a black bra with wide set straps and low cut cups that would show off the tops of my breasts. Finally I put on the black georgette print dress that I had loved so much when we were buying clothes. It showed just a hint of cleavage. I sat at the dressing table and did my makeup and settled the wig on my head. I stepped into the sandals and walked to the full length mirror to check my appearance. Mother was going to get a real surprise.

I packed a couple of changes of clothes in a small bag and locking the apartment, went to my car. The drive home was uneventful although I did notice a couple of young men checking me out when I stopped to buy fuel for the car. An hour and a half up the interstate and then another twenty-five miles on a winding two lane road up the mountain and through farming country to the small town where I was born and raised.

As I approached my home town I began to wonder just how I should proceed. Should I drive to the back of the house and just walk in through the kitchen door like I normally would? No, seeing a "strange" woman, unannounced and uninvited, in her kitchen would probably upset Mother. I parked in the drive near the front of the house and climbed the three steps to the front porch. I rang the bell. Mother came to the door studying me through the storm door to see who I was. She unlatched the door and opened it a few inches and said, "Yes?"

In my normal masculine voice I said just one word, "Mother."

Her eyes widened and she studied my face intently for a moment and then said, "Carl?"

"Yes, although people call me Cheryl when I'm dressed like this."

She pushed the storm door open wider and said, "Well, come on in." As I stepped into the house, Mother put her arms around me and hugged me. I hugged her and kissed her on the cheek. "You certainly look nice. I assume this means that you are living as a woman all the time now."

"Yes I am. And that is why I wanted to come and talk with you."

"Come on back to the kitchen. Would you like a cup of coffee?"

"That sounds good." She poured two mugs and we walked into the den. I sat my mug on a small table beside an over stuffed chair, turned and ran my hand down my skirt to pull it forward as I sat being careful to keep my knees together. Mother sat in her favorite recliner.

She took a sip of her coffee and said, "Well, you certainly look different than when I saw you last."

"But you knew that something was going on, didn't you?"

"Oh, yes. When your boss, Ellen Brown isn't it, came to talk to me she was very persistent in her questions about your wearing women's clothes. She assured me that was actually a point in your favor and certainly would not count against you. I really wondered how much I should tell her. So I didn't say much. I just acknowledged that I knew that you had been wearing Ann's clothes and sometimes mine. She didn't press me any farther than that. I wondered just what she was after but she seemed satisfied with just that much information."

"Well, just how much more do you know?"

"You regularly found reasons to be home alone. And there were usually signs that you had been into our clothes. I know you thought you were careful, but you weren't that careful. Ann and I talked about it from time to time. We agreed that as long as you weren't damaging the clothes it was easier to let you alone. I thought about getting you your own dresses and underwear but decided not to. I didn't want to encourage you."

Just then I heard the back door open and Ann's voice. "Hello, Mom? I'm home. What's with Carl? He left his car blocking the drive?" Just then she walked into the den and saw me. "Oh, excuse me. I thought that was Carl's car out there."

I stood and walked toward her. "It is," I said.

Ann did a quick double take and said, "So you have finally come out of the closet, huh, little sister?"

We hugged and kissed each other on the cheek. "Well, I have to say, you do look nice," she said.

Mother stood and hugged Ann. Then she stepped into the kitchen and returned with a mug of coffee which she handed to Ann and asked, "How was your trip?"

"Oh, the traffic coming out of Atlanta was beastly. But then, it always is." Ann sat in the wicker rocker and crossed her legs. She was wearing sandals with 4 inch heels, jeans, a tee shirt and had her hair pulled back in a pony tail.

Ann looked at me and asked, "What brings you here all dolled up like that? I didn't think you were the kind to go running around in public in a dress."

"Well, I haven't been until recently. And that is what brought me here. I need to talk to Mom, and you too I guess, about what's happening to me. You know where I work. About a month ago they began to talk about going to the national convention. When I said that I didn't think I would fit in they said, 'Why, because you are a male? We will help you go as a woman.' When I agreed I got a two week crash course on being a woman - clothes, makeup, speech, gestures, the works. I even have a different apartment in a neighborhood that is safe for a single woman. All my male clothes are packed away. And I started going to work every day in a dress. They all treat me like a woman at the office. Everyone calls me Cheryl. Somehow, I think I've lost control of my life. I don't think I could go back now, even if I wanted to. And I don't know if I want to or not." I was on the verge of tears when I finished.

"You poor dear. I don't know what we can do to help you right off hand. But I'm glad you felt that you could come talk to us."

Ann asked, "How did you feel about all this from the beginning?"

"I was flabbergasted at how much they knew about me. I didn't think anyone but you knew about my wearing a dress occasionally."

"It really was more than occasionally, wasn't it?"

"Well, yes. But still, I didn't think anyone knew. But then when they offered to help me, it seemed like a dream come true. Liz and Sandra helped me buy clothes and makeup. Renee coached me on my speech and gestures. They gave me a raise last pay period. I was going great guns. Then all of a sudden, when I moved to the new apartment I began to have second thoughts. That's when I called and said that I wanted to come home today."

"But you came in a dress."

"I debated about that a lot this morning. But I decided that with my eyebrows plucked and my nails painted, I really couldn't convince anyone that I was a boy. So it kind of became the course of least resistance."

"And you don't have any fear of being found out?"

"Not much. I have been wearing dresses and working very hard on looking and acting like a woman lately. Under normal circumstances, I don't think anyone would notice."

"I've noticed that even here with us your gestures and even your voice seem feminine. You've really gotten into this."

"Well, tell me, Honey, how long will they expect you to wear a dress? Can you stop once the convention is past?"

"I really don't think so. Now that I am in a dress, I think Ellen will want to keep me in one. It looks better to the organization if everyone in the office is a woman. And we do have visitors from other offices from time to time. They really only put up with Carl because they couldn't get a woman for the job. And now that they have Cheryl, I don't think they will let her get away."

Ann looked at her watch and said, "It is almost noon. Let me slip into a dress and we can go to the Chinese buffet for a bite of lunch. But I can't let my little sister out shine me."

Mother went to her bedroom to put on a nicer dress and I went to the half bath off the hall to check my makeup. In a few minutes both Ann and Mother returned. Ann had put on a dress and significantly upgraded her makeup. She was serious about not letting me out shine her.

I moved my car to its usual parking place behind the house, carried my bag into the house and hung the clothes I had brought in my closet. We all went to the restaurant in Ann's car. As I climbed into the back seat I realized that there really is no graceful way to get into the back seat of a two door car wearing a skirt. In the process I carelessly exposed a lot more of my breasts than I should have. Ann saw and said, "You will have to tell me about that later" as she made a gesture indicating what she had seen. Mother was getting in and apparently missed that bit of conversation. And I was glad for that.

When we got to the restaurant I remembered to put my hand up to hold my dress and not expose as much breast as I got out of the car. Mother was holding the door and watching. She imitated my gesture and nodded her approval.

While we were at the salad bar I noticed that Ann was talking to Clint Adams, a boy we had known since middle school days. He had gotten one of the few good jobs in town and stayed while most of us went off to larger cities to go to school and look for work.

As we ate Ann chattered about her latest boy friend. She seemed to thing he was a really nice guy and she hoped that the relationship would progress into a serious romance. Then as we returned from getting our deserts she asked me, "And what about you? Have you found a boyfriend yet?" She gave me a wicked little grin and winked.

My face felt hot. I must have blushed beet red. I knew that Ann was just teasing but it still got to me. I tried to gather my composure and replied, "Nothing serious yet. Although I do have a couple of prospects." Fortunately, Mother understood the exchange and didn't take it seriously.

"Clint just asked me for a date for tonight and I told him my cousin was visiting from Birmingham. He said that was no problem, he could arrange for a double date. He will call later this afternoon to confirm it."

"Thanks, just what I needed. Someone to start playing matchmaker," I said sarcastically.

"No, I'm not playing matchmaker, Sis. I just want to help you see how the other half lives. Then you can make a better decision about what you want to do."

"That seems like a good idea, Cheryl. Go and enjoy the experience. See if it is what you want to do for the long run," said Mother. Mother had called me Cheryl and seemed to do it as naturally as if she had called me that all my life.

Just as we were ready to leave, Clint came to our table and introduced himself to me. Although I had known him for years, he obviously didn't recognize me and I played like I was meeting him for the first time.

Ann paid our bill and we stopped at the ladies room to check our makeup. Neither Mother nor Ann seemed the least bit surprised that I went right in, went to a stall, closed the door and did my business. When I finished I joined them at the mirror and refreshed my lipstick. As we left Ann commented, "You certainly seemed enough at ease in there."

"I've gotten a lot of practice lately."

When we got back home, Ann parked beside my car behind the house and we went inside. We returned to the den and I review the previous month in detail so that Mother and Ann would understand just what I was involved in.

After a while Ann said to Mother, "Would you excuse us please? Cheryl and I need to have a little sister to sister talk." We stood and I followed her into her bedroom. She pushed the door closed and turned to me. "All right, kid, come clean. There is a lot more to you than you are letting on. I saw when you got into the car. That isn't just a padded bra you are wearing. And I've studied your figure. Carl never had as much hips and tail as you have. What have you done? Implants?"

"Sis, I'll bare all if it won't embarrass you."

Ann sat on the bed and said, "I'm waiting."

I unzipped the dress and slipped it off. I laid it on the bed and removed the half slip.

"OK, now I can see that you are wearing a padded panty. That accounts for the hips and tush. But I still want to know about your boobs? How did you manage those? And that very flat front? There is no bulge there."

I stalled about the breasts by asking, "Did you ever hear of a gaff?"

"A what?"

"A gaff. It's a garment that pulls my genitals up and back so that they don't show."

"Oh. Isn't that uncomfortable?"

"To tell the truth, yes. But I've gotten used to it."

"OK, quit avoiding my question. How do you manage boobs that look so real?"

I grinned and unfastened my bra, giving her a full, unobstructed view.

"You're still holding out on me. What have you done?"

"It is just a matter of silicone and glue. They are called prosthetic devices. And they are generally sold to women who have had a mastectomy. Here, you can feel of them. If you look closely, you can see the seam where they end. I have covered it with makeup but it isn't ever very obvious."

She touched and felt and said, "Even nipples that look real enough to suck." She pinched a nipple.

I didn't feel anything, of course. But I swatted at her hand and said, "Stop that! You're hurting me!" Then we both giggled and fell into each others arms.

I picked up my bra and put it back on. Then I said, "If you will loan me a robe, I would like to get comfortable for a while." I slipped on the robe she handed me, turned my back to her and removed my panties and the gaff which I handed to her to examine as I replaced my panties.

"Now come and sit beside me little sister. There are still some things I need to know that you may not feel at ease discussing in front of Mother." I sat beside her on the bed and she continued. "Be honest with me. Tell me about your sex life. I know you didn't date much in high school. What's your preference? Boys or girls?"

I scowled at her and hit her on the shoulder playfully as I replied, "Girls! It is now and always has been. But you know that I have always been a bit shy. Consequently, I haven't had a lot of experience. The twist is that I also like to wear girls clothes." She nodded. "Now, don't ask me why. I don't know. I am not homosexual and have not interest in a sex change. It is just one of those things. Dresses feel good."

"I've had several girls and women that were good friends but I've never found the one that I wanted to get serious about. And if I did find her, how would I tell her about my hobby? I really doubt that I could give it up. I'm addicted. Liz at the office looks after me like a mother hen caring for her chick. But that is not what I'm looking for. Besides, she is as old as mother.

"This thing where I am working now has really thrown me for a loop. They have more than just accepted me. They have encouraged me and actively helped me. And I'm not sure what all their motives are. I get the impression they were looking for a crossdresser as much as for a person with my skills. And then there is the matter of about $2,000 that I have spent for clothes, makeup, a wig and the prosthesis. This gets to be an expensive hobby.

"Boy, that must be some wardrobe you bought!"

"Its not the clothes, although I did spend more than I wanted to on them. But you have seen where a big part of the money went. A good wig and the prosthesis cost a bundle."

"Yeah, I can imagine. Now level with me. While they were helping you buy clothes and teaching you about all this stuff, what else did they teach you? You know, like about sex?"

I grimaced. She was really pinning me down and responding "nothing" wasn't going to satisfy her so I decided to tell the truth. "Liz figured out that I didn't have much experience so she taught me how to really satisfy a woman as a man and then as a woman."

"Wow! Double play!"

"I guess you could say that. Now, tell me about this double date you have arranged. Liz didn't teach me how to deal with a man. And I'm not interested in 'satisfying' one," I said.

"Well, there is a good looking girl visiting me this weekend. It would be rude for me to go out and leave her sitting home," she grinned. "And I truly believe that you need to have the experience of dating a boy to see how they behave and what it feels like to be a girl in that situation. We will go for dinner and dancing. There may be a little kissing and petting but I promise that I will not let it get out of hand and let you be embarrassed. Just go with the flow and whenever you get uncomfortable, call a halt."

"You make it sound so easy."

"It is easy. Girls really control the situation. You can do as much or as little as you want unless it comes to rape. But Clint is not that kind of guy and I don't think he will bring along anyone who is."

I went by my room and changed from the high heeled sandals to a pair of flats. Then we returned to the den and visited with Mother until time to get ready for the evening.


Chapter 9

The Date


Almost two hours before the time for the fellows to pick us up Ann said, "We'd better start moving around to get ready. Come on, I know just the outfit for you to wear tonight."

I obediently followed her to her bedroom. She opened the closet and took out an outfit that was one of my favorites. She said, "You like this, I know. You have worn it several times. But I have never seen you in it. So tonight I'll get to see you."

The outfit was a crisp white cotton blouse that buttoned up the front with a collar that opened to a deep but narrow V. The collar rolled out to the side rather than lying flat. It was trimmed along the edge of the collar and around the short sleeves with royal blue that matched the skirt. The skirt was long, a little below mid-calf. It buttoned down the front with large buttons. Although there were buttons all the way down, the button holes were sewn closed from above the knee on down. It was obviously meant to show leg especially when you sat.

"O o oh, I do really like that outfit."

"Ok, if you look as good as I think you will in it, its yours to keep."

I carried the dress to my room and began to prepare for the evening. I removed my wig and cleansed my face. Then I applied moisturizer. After my bath I pulled on the gaff, white padded panty and a white bra that showed plenty of cleavage. I sat on the bed and pulled on nude pantyhose. I pulled on a mini-skirt length half slip and slipped my robe back on.

Since my room, being a boy's room, didn't have a dressing table or even a good mirror, I gathered up my makeup and padded over to Ann's room. I tapped gently on the door and heard her say, "Come in."

I pushed the door open and stepped into the room. Ann was just coming out of the shower. She had a towel wrapped around her body but she dropped it and reached for the panties lying on the bed. I blushed and said, "Excuse me!"

She looked at me and grinned. "What's wrong with you. You're a girl now. You have to get used to seeing other girls in the buff. She turned and walked over to me hugged me and kissed me on the lips. I could feel her bare body pressing hard against me and I felt excited.

"Hey, stop that! You aren't supposed to do that with me."

"What, hug a girl friend? Why not?"

"Oh, come off it Sis. You know what I'm talking about."

"Sure, but I wanted to see your reaction. Now, what did you want?"

"I need to use your dresser to put on my makeup. I don't have a decent place in my room." I put my makeup down on her dresser, sat and began to put on my makeup. But I couldn't help watching Ann in the mirror as I worked. She did a striptease in reverse. It drove me crazy.

I gathered up my stuff and returned to my room to put on the dress and wig. I stepped into my shoes, black pumps with 3 inch heels, and returned to Ann's room to adjust and fasten the wig. Ann looked me over and said, "You look very good in that outfit. Its yours. Say, don't you have shoes that match?"

"No, silly. I didn't even have this outfit until a minute ago."

Ann reached into her closet and pulled out a pair of royal blue pumps that matched the dress perfectly. I tried them on but they were too tight.

"Wait a minute. I think Mother used to have a pair of shoes this color and her feet are a little larger than mine." She left the room and I heard her talking to Mother. In a minute she returned with a pair of pumps the right color with 2 inch heels. I slipped them on. They fit nicely.

When the fellows arrived, Mother let them in at the front door and led them back to the den. Clint introduced his friend, Mark Watts. Mother made small talk with them for a minute or so while Ann and I put on the finishing touches and spitzed on perfume. We checked our purses to see that we had documents, lipstick, tissues and some money. Ann reminded me, you never go out without enough money to get home by yourself if necessary. Then we walked out to met them. Clint introduced Mark to me. He must have been at least six feet two inches, a couple of inches taller than Clint. He seemed very nice. Like good girls, we told Mother where we planned to go and when we expected to be in. She reminded us to come in quietly since she would probably be asleep by then.

We walked out to the car. It was another two door and Clint was driving. I negotiated entering the back seat as gracefully as I could and moved to the left to make room for Mark. He climbed in. Then Ann sat in the front and pulled her seat forward a little to make room for Mark's knees. Clint closed the door and rounded the car to get behind the wheel. We went to a supper club about 20 miles away, on the edge of a neighboring town.

As we ate Mark asked me about my work. I told him I was a database manager for an NGO. "A what?" he asked.

"A Non-governmental Organization."

"Oh. What does the organization do?"

"We promote women's health and safety issues both here and in other countries."

Then I asked about his job. He readily launched into a detailed discussion of his work as a supervisor for the local power company. That got us through the meal with no further discussion of my job. As we finished the meal Clint suggested that we have a glass of wine.

Ann responded for both of us. "Thanks, but we don't drink. And if you have more than one glass, which one of us do you want to be the designated driver?" She grinned as she said it but Clint got the idea. He didn't order wine and nothing was said about drinking the rest of the evening.

The band had already started before we finished dinner. As the waiter cleared away the dishes Mark looked at me and ask, "Shall we dance?"

He led me to the dance floor. The first couple of songs were fast so we stood facing each other and each did our own thing. I was thankful for the lessons from Liz. Otherwise I would have looked really bad. I smiled at Mark and said, "I'm not much of a dancer."

"Well, I'm not either."

Just then the music changed to a slow number. Mark offered me his hand and placed his other hand on my hip. "This is more my speed," he smiled. And it really was. He was a good dancer and made me feel at ease dancing with him. As we danced we talked about college and how he came to live in a small town like ours.

The slow dance ended and Mark led me back to the table. He order soft drinks and we watched Clint and Ann dance. They both obviously enjoyed the fast dances. After several songs the band played another slow number and we returned to the floor. This time Mark held me closer and I was obliged to put my arms around his neck. I felt his face in my hair. I looked up at him. He moved his face down slightly and kissed me on the lips. I was surprised and must have stiffened slightly because he sensed it and said, "You didn't like that?"

"Its just that you surprised me. I wasn't expecting it." We danced on. I looked up at his face and this time saw it coming. There was nothing I could do except close my eyes and accept his kiss. It was tender and did not linger.

Finally, when Clint and Ann sensed that Mark and I weren't enjoying the fast dances, Clint suggested that we leave. As we left the parking lot Clint turned left instead of right, toward home. In a few minutes I realized where he was headed. I had taken a girl or two there myself. We stopped at an overlook where we could see the valley and the moon reflecting off the river below. It was a beautiful sight. We stood at the protective rail and looked out across the valley. Mark put his arm around me and pulled me close to him. I didn't resist. Then I felt his hand move up under my arm and I knew even though I couldn't feel it that he had put his hand on my breast. I reached up with my other hand and gently moved his hand down to my waist. Then I looked up at him and smiled. He looked like a little boy who had been caught with his hand in the cookie jar. I stood on tip-toe and kissed him on the cheek. He responded by turning toward me and took me in both arms and kissed me passionately. I tried to find a neutral response, neither pushing him away nor being too willing to continue.

I looked over at Ann and Clint. They were locked in a passionate kiss. Clint obviously had his hand on Ann's breast. I turned back to Mark and we kissed again. After several minutes I coughed and said, "I think we had better go." Ann heard me and broke off her kiss with Clint. We got into the car and returned home. Although there was no way I could keep from exposing a lot of leg with the skirt I was wearing, Mark was gentleman enough that he didn't try to put his hands on my legs or do anything more aggressive.

At the house Mark walked me to the door and once more pulled me close for a kiss. I kissed back and when it ended thanked him for a lovely evening. He said, "I hope that I can see you again when you visit here."

I gave him a final kiss and stepped inside the house. I gently pushed the door closed and let out a sigh of relief. I had survived. But I knew that was not something I wanted to make a habit of.

I had slipped out of my shoes and picked them up but was still standing just inside the door when it opened and Ann stepped in. She followed my example and slipped out of her shoes. As we walked quietly down the hall to her bedroom Ann put her arm around my waist and pulled me close. I felt her hand move under my arm and I knew that she was putting her hand on my breast. She opened the door to her room, pulled me in and quietly closed the door. Then she turned and kissed me passionately. Her tongue probed my lips and pushed into my mouth. I kissed back.

"Let's clean off our makeup. Then I want you to show me what Liz showed you," she said.

The next morning was Sunday. As we ate breakfast Mother asked, "Did you have a good time last night?"

Ann immediately responded, "Yes, we had fun."

Then Mother looked at me and asked, "Did you enjoy being kissed?"

How do mothers know so much? "Well, I managed not to gag and did my best to accept it as part of the way things are right now. But I confess to no enthusiasm for it."

"She's not into heavy petting if that's what you mean," Ann said with a giggle.

Mother just nodded and went on eating.

After breakfast we dressed for church. Ann loaned me a red coat dress that came to my ankles. It had a sailor collar with white trim. Although it was almost straight, darts did shape the bust line and a placket in the back pulled the waist in some. She wore a teal suit. The skirt came to her knees and the jacket flared over her hips. Mother wore a sleeveless floral print shift that came to just below her knees. Over this she put a solid short sleeved jacket that matched the basic tone of the dress.

As we left the church we spoke to the minister and complemented her on her sermon. Then we stood outside for a few minutes and chatted with people. I was introduced as Mother's niece from Birmingham. I already knew most of the people but they didn't recognize me. Then we moved on to a local restaurant for lunch.

As we ate Mother asked, "Well, Honey, have you made up your mind what you want to do?" I don't remember Mother ever calling Carl, Honey.

I thought about my answer a bit and then responded, "It seems that I have little choice except to continue as I am for the time being but before I have to start buying winter clothes I will have to make a decision. That gives me about three months. Now, let me ask you a difficult one. If I decide to go back, the transition will not be as quick and easy as it has been up until now. It will

take time for eyebrows to grow and to get rid of these acrylic nails. If I were without work for two or three months, could I come back and live here?"

"Cheryl, you know either you or Carl are always welcome here."

"Thanks, I appreciate that."

Back at the house we changed into more casual clothes. I put on a short sleeved v necked blouse and a jeans miniskirt that Ann gave me. She also gave me two other skirts and three blouses. As she handed them to me she grinned and said, "its not like you haven't worn them before."

I blushed and said, "That's true. But I didn't think you knew."

"That's OK. I'm not the jealous type. At least I wasn't, but now that I've seen you, I might be more jealous." She kissed me on the cheek. Then she pulled me to her and gave me a deep passionate kiss.

Ann left first since she had farther to drive. We hugged and kissed each other on the cheek. She kissed Mother and left.

We sat and looked at each other for a few minutes. Then Mother said, "Somehow, I'm not surprised at this turn of events. You were always too sweet and docile a child to be a boy. Oh, you played with the boys and in high school you ran track and were on the swimming team, though you didn't excel in either. No, I'm really not surprised. Are you thinking about going all the way and have gender reassignment surgery?"

"No, I've never considered that. I like the way I am too much."

When it came time to leave, I carried my bag to the car and then walked back to the kitchen. We stood by the door for a couple of minutes in silence with our arms around each other. Then Mother said, "Take care and don't let those women push you farther or faster than you want to go. Remember, it is your life and you are the one that has to live with the consequences."

"I will, Mother." I kissed her on the cheek, gave her a tight hug and went to my car. Mother understood and whatever she may have felt wasn't important at that moment. She was just taking care of her child.


Chapter 10

The Dates


Monday morning I awoke to a slow steady rain. Normally, that wouldn't be a problem because I really like a slow rain. But neither Carl nor Cheryl have a raincoat or umbrella. Carl would slip on a waterproof windbreaker and a baseball cap and run for it. But somehow that didn't seem like a good option for Cheryl. I made some adjustments in the clothes I had planned to wear, choosing a knee length skirt that would be washable if it got wet and flats. Then I slipped my

heels and an extra pair of hose into my purse. Finally, I took the largest plastic bag I could find, cut it open down one side and placed it over my head and shoulders. I dashed to the car as best I could and from the car to the office. Aside from a few splatters of muddy water on my hose and a few drops of rain on my skirt, I managed OK. A quick change of hose and shoes at the office and I was ready for the day.

I watched the others arrive and studied their rain gear. Most used umbrellas and didn't fare any better than I had. Two had lightweight raincoats. But they still got their legs and shoes wet. I made a note to buy an umbrella.

I had finished all the preparations for the convention as Carl - reports, graphs, even a Power Point presentation in case I was called on to make a presentation of my work. The reports were sent to national headquarters to be included in the handouts for the convention. There were no fund raising projects in the works and generally everything was slow. That left me pretty free to work with Renee to prefect my image and prep for the convention.

Whenever Renee said that she had the time, we would go to the conference room and practice. Besides my voice, walk and gestures, Renee suggested that I needed to rehearse some stories about my experience with men. Women always talk about this guy they had dated and that guy they had dated, she said. Therefore I would need some stories to tell. I spent one evening reviewing my dating experience and making notes as to how to see it from the girl's point of view.

Then I added things that I had heard Ann talk about. When I looked at her stories, I realized just how limited my experience really was. The next day I had five good little stories to tell. Renee was satisfied that they would do since I admitted to coming from a small town where I had led a quiet life.

Renee insisted that I needed more feminine experiences so that I would be at ease in any situation. We went "shopping" on office time. We didn't buy much but we looked at lots of dresses and discussed their cut, the type of fabric and color. I even tried on a few. We looked at jewelry and lingerie. I did buy a couple of pair of shoes and purses in colors to match some of the outfits I had.

On Wednesday Renee noticed that I was wearing an outfit that was not one we had bought that first Saturday. "Hummm. Been shopping have you?"

I grinned and said, "No, when I went home last weekend my sister gave me several outfits that she knew I liked."

"You went home in a dress?"

"Well, there really wasn't much of any other way to go. I couldn't grow eyebrows just for two days nor could I remove these acrylic nails. Mother was a little surprised but not too much. Ann came in from Atlanta and we had a great weekend together. Lots of girl talk," I laughed.

"I gather, then, that they are cool with you dressing like this."

"Yes, I think I have the full support of both of them. Ann said, 'So you have decided to come out of the closet, Sis.' And Mother said, 'Cheryl or Carl is always welcome here.' I guess I could hardly get more support than that."

"That's good. Having a sympathetic family is really nice. And did you date while you were there?"

Some people can be so nosey! "Yes, Ann arranged a double date for Saturday night. She went with a boy we have known for years. She introduced me as a cousin from Birmingham and he didn't recognize me at all. I went with a fellow that is new in town."

"And. . ."

"And what?" Although I knew full well where she was heading.

"And did you like it when he kissed you?" I must have blushed. I seemed to be doing that a lot lately. Renee giggled. "Men always kiss their dates."

"No, I didn't like it. But I tried not to show it. He was a good guy, though. He mostly kept his hands to himself. And I didn't want to be mean to him."

"So you like kissing women better?"

"Absolutely. I like to wear dresses but I'm not a homosexual."

"Show me."

Renee moved closer and I pulled her to me arms and our breasts collided as I kissed her hard and pushed my tongue into her mouth. At the same time I put my hand on her breast and began to rub her nipple.

When we parted Renee giggled and said, "I'll take that as proof, for now. But you need more experience with men. I'll have to arrange some dates for you."

"Thank you, but I'm old enough to take care of myself."

"Not in this role, your not. Take it from me. You need more experience. I'll arrange a couple of double dates for us and you will learn to enjoy being a girl, even kissing the boys."

"That's what I'm afraid of."

At break time Ellen announced that she had made room reservations for four nights and that we should pair up and tell her who we would be sharing with. After break I went by her office to ask about my situation. "Oh, you are already spoken for. Renee said that you two would be together." She gave me a knowing smile.

Renee was as good as her word. On Thursday she announced that we had a double date for Friday night. We were going to the movies. The show she had chosen was "Dr. Doolittle Talks to the Animals." Not the sort of thing I would have chosen but then, maybe she had method in her madness.

Friday afternoon I got out of the office promptly at 4:30 and headed for home wondering what was in store for me. I had a snack and then went for a long soak in the tub. At least it soothed my nerves some. I got out of the tub and patted myself dry. Then I began to think about what to wear. Renee hadn't made any motherly suggestions. I decided on a pink v necked sweater and jeans skirt that came to mid-calf. But first came white lace trimmed panties and the ever present padded panty. Next I put on nude pantyhose. I chose a white bra with wide set straps that left the tops of my ersatz breast exposed and pushed them together to show cleavage. Then I put on the skirt and sweater. Once I had my clothes on, I sat at the dressing table and began on my makeup.

I had been confident that Ann would not knowingly put me in a situation that would be dangerous or that I couldn't handle. And she would help me out if need be. However, I did not have that same confidence in Renee. I had to hope that she wouldn't risk messing up lots of things by making a poor choice for my date.

But there was no easy out so I began applying my makeup: foundation, powder, blush, eye shadow, eye liner, lip liner and lipstick. Finally, I settled the wig on my head and pinned it in place.

I chose a diamond pendant necklace and couple of rings for jewelry.

Renee and her friends were right on time. I greeted Renee with a kiss on the cheek and she introduced her two friends, Harold and Wallace. "My friends call me Wally," he immediately volunteered. So Wally it was.

We walked out to the car which was a four door. The fellows held the doors for us and then went around to get in on the other side. Wally was a joker. He found something funny in almost everything that was said or that we saw. And his language was not appropriate. It was just plain crude at times. He also had roaming hands. Before we got to the theatre I knew that I was in for a battle all night long. In the car he almost immediately moved over close to me and put his hand on my leg. In the theatre he put his arm around me and very soon had his hand on my breast. Fortunately, I was aware of his move and met his hand with mine and gently moved it back up on my shoulder. And that kind of struggle continued all evening long. When we got back to the apartment he walked me to the door while Renee and Harold waited in the car. He had his arm around my waist and I felt a kiss coming on but I managed to make a quick move and kissed him on the cheek, thanked him for the lovely evening and turned to put the key in the lock. He was obviously disappointed. And I was relieved to be inside the door alone.

Saturday morning I called Renee. "Just what were you thinking, fixing me up with a date with that clown? I had a terrible time. I had to fight him off all the time. If that is what you call more experience with men, I don't want any more."

Renee laughed. "You didn't see the struggle that I was having. Harold was no different. He was just less vocal. But I had a fight on my hands all evening long. You may not have liked it, but you got the kind of experience that goes with being a woman. It isn't all about being treated like a princes. Sometimes it's a fight."

"OK, but don't do me that way again or so help me, I will walk out on him and let you explain."

"Well, I do know some men who are neither as loud and foul mouthed nor as aggressive. That doesn't mean that they won't try to get in your panties. They are just nicer about it."

"Does that mean that you don't know any gentlemen?"

Renee laughed at that. "Maybe one or two. But I'm saving them for myself."

The convention was Thursday and Friday in Las Vegas. Tuesday evening I packed my bag. Wednesday we wrapped things up at the office and closed at noon. I had been back at my apartment only a few minutes when Renee arrived. I put my bag in her car and we went to the airport. Check-in was easy and I was glad that I was not singled out for more intensive scrutiny in security. We all boarded the Southwest Airlines flight and had seats close together. As we checked in at the hotel Ellen said, "Remember, the meeting starts at 9 in the morning and everyone should be in their places. Enjoy yourselves."

Renee and I went to our room and unpacked. The room was large with two queen size beds. We checked the entertainment guide and picked a show to attend. After the show we returned to the hotel and Renee got further proof of my sexual orientation.

Thursday morning we got up early to be dressed and ready for the day. Renee told me that these two days would be big dress-up days. "You know, women really dress for other women more than for men," she grinned.

After my shower I slipped on black panties and the padded panty. I put on navy pantyhose. I put on a white bra and cami. I did my makeup carefully both to do the best and to avoid being overdone. Then I fastened the wig on my head and gave it a few touch-up strokes. Finally, I put on the white blouse and blue skirt and jacket from the mix and match set we had bought the very first day. I stepped into my pumps and walked to the mirror. I really felt good about the way I looked.

We had a light breakfast in the hotel dinning room and then returned to the room to check makeup and get our material for the convention.

As we were walking through the hotel lobby on our way to the meeting hall I heard someone call my name. "Cheryl! Cheryl McArthur! What are you doing here?" I turned and looked toward the voice. There stood Mark and Clint all dressed up in suits and looking like what they were, young engineers on their way to an important meeting.

Instinct told me what to do. We walked quickly toward each other and I accepted a hug and kiss on the cheek from each. Then I explained, "We're here for our organization's annual convention. And you guys? What are you doing?"

"We're here for a symposium on alternate energy sources. We'll be here until Sunday afternoon."

"Great! We're in room 873 and we will be free evenings." Ooops. Had I said too much? "Oh, excuse me. This is Renee Hamilton. We're rooming together this week."

"OK, we're on our way to the meeting now but we'll be in touch." Then Mark pulled me close and gave me a quick kiss on the lips.

"Wow! You do all right!" Renee was grinning from ear to ear. "You did all the right things and I'll bet we'll get a call from them this evening."

We continued on to the convention. It wasn't a large gathering, probably less than 300 women. But all were dressed and made up to the teeth. It really was true what Renee had said, women dress for other women. The meeting was a lot of talk emphasizing the things I had already read in the literature of the organization.

After a buffet lunch served in a room just off the meeting room we divided into smaller groups according to our jobs or interests. My group was all technicians - computer literate women who also had a lot of savvy about fund raising. It was mentioned in the meeting that I had done much to improve the record of our office. But it was clear from the discussion that I had a lot to learn about how to get people to open their wallets.

The meetings broke up about 4 pm and we returned to our room. True to Renee's prediction, when we came by the desk on our way to the room we found that we had a message inviting us to dinner and dancing that evening. We acknowledged the invitation when we arrived in the room. After a shower and a quick nap I looked through my wardrobe for something to wear. I chose a black drape-neck dress with spit flutter sleeves and an inverted v notch in the hem. The dress was lined but only to mid thigh. The skirt below that was semi-transparent. This was sure to get some attention.

The fellows were waiting for us in the lobby when we arrived. We went to a "dine and dance" place that served excellent steak. I had to really restrain myself to eat like a lady and not try to match Mark and Clint. The band started even before we finished eating. As the waiter was clearing the table and asking about dessert, Mark asked me to dance. It was a slow number so we both enjoyed the dance. He held me close and put his face into my hair. I felt his hand slide down from my waist. Then I lost the feel and I knew he was on the padded panty. When the dance finished he kissed me gently on the lips.

Back at the table we ate our desserts and watched Clint and Renee gyrate to a fast dance. I looked at Mark and he just shook his head. "That isn't dancing to me," he said. And I nodded in agreement. I had guessed right. The dress was getting attention. I felt Mark's hand on my leg. I didn't move it away immediately. I let him enjoy the feel of the nylon of the dress rubbing against the nylon of my hose. I was enjoying it too. We danced several more slow dances and a couple of the fast dances then we headed back to the hotel.

In the car Mark put his arm around my shoulder and pulled me close. I didn't resist. As we pulled into the parking deck he kissed me firmly on the mouth and I kissed him back. Then I realized that his hand was on my breast. I gently moved it away and smiled at him. He smiled back and kissed me again. He walked me to the room. I thanked him for a lovely evening and kissed him good night, unlocked the door and stepped inside.

In a couple of minutes Renee came in. She said, "You do all right. You're just nervous about all this because you are new at it. But with more time and experience you will be fine."

"But I'm not sure I want more experience."

"Well, you sure couldn't tell it tonight. Mark was well behaved but you weren't putting up any resistance." And I had to admit to myself that what she said was true.

Friday morning I decided to go with a scar/skirt set with a double-button front jacket. The jacket was a pale avocado and the skirt and scarf had a yellow and pink floral print over a very light avocado background. The skirt was pleated all around.

The meetings Friday were more or less a repeat of Thursday. At the end of the day we hugged those with whom we had had more contact and promised to keep in touch.

For Friday evening I chose a sleeveless black dress with white dots and topped it with a black short sleeved jacket that just flared at the hips. We went to one of the topless shows. Although the girls were topless, it really wasn't the sexy thing that I had imagined. Just a lot of feathers and colored lights and half-dressed women running around. On the way back to the hotel Mark and I did some mild petting but I tried to be careful not to lead him on or to let him explore too much.

Saturday morning we lounged by the pool. I had carefully chosen a one piece suit that would pretty well hide the inevitable bulge in the groin. But there was no way I could manage a padded panty under the suit. Besides, the pads would have been too obvious. I didn't swim because I couldn't afford to get the wig wet. Mark and Clint came by and promptly dived in. Then they swam back to the edge of the pool near us and splashed water at us like a couple of teenage boys. When it was apparent that we weren't going in the water they came and sat beside us.

We chatted about schools and jobs and family and home towns. I was really skating on thin ice in that conversation because Clint knew too much about my background for me to just assume Carl's history. But I managed to get through without getting called on anything.

As we left the pool we told the fellows we were going shopping in the afternoon. Then Mark said that he wanted to take me to dinner and a special show. Clint said he would take Renee to another.

Renee and I shopped for a while and then returned to the hotel to rest and bath before the evening.

I dressed in black panties, the padded panty, black pantyhose, a black bra and half slip. I pulled on the Georgette dress that I loved and set about doing my make-up for evening. I applied foundation, set it with powder, applied blush and green eye shadow to match the green print in the dress, mascara, lip liner and lipstick. Then I seated the wig on my head and fastened it. Mark had been secretive about what show we would attend but I figured the Georgette dress would be good anywhere.

Mark called for me at 6 and we had dinner together. Then we drove to a theatre that I had heard about but hadn't had opportunity to attend. The show was a transvestite review. The singing and dancing was spectacular and it was hard to believe that the "girls" in the show were really men. But then, what was I doing? Asking all who saw me to believe that this man was a girl.

As we drove back to the hotel after the show Mark tried to draw me out about female impersonators and transvestites. I was amazed at how knowledgeable he seemed. And that he didn't make any harsh or critical remarks about them. We stopped in the parking deck. Then Mark turned and put his arm around me and pulled me to him for a deep passionate kiss. "I'm jealous of you," he said.

"Jealous of me? What do you mean?"

"I'm jealous that you are able to do what I would love to be able to do but can't."

"I don't understand. What are you getting at?"

"You are a guy but you do a fantastic job of seeming to be a woman"

My mouth fell open. I didn't know what to say. Finally, I gathered my self together and ask, "What makes you think that I'm not a woman?"

Mark smiled a little and said, "I guess you would have to say, 'it takes one to know one.' I like to dress up but I could never pass in public. But the knowledge and the experience that I have because of that helped me see things that other people probably wouldn't notice. I picked up on the wig the first time we dated. And since we were dancing last night I have been testing you in little ways. I felt the padded panty. I realized that your breasts must be false because you didn't react when I pinched them one time. Then, when I saw you in a bathing suit this morning, all my suspicions were confirmed. The suit was much too modest for a nice looking woman like you to wear unless she was hiding something."

Then he pulled me to him again and said, "Now, let me treat you like the woman you are." And he kissed me again, pushing his tongue deep into my mouth. As he did, he ran his hand up my leg under my skirt. I put my hand on his and stopped him. Then I pushed away gently.

"Easy, Mark! I'll have to admit, you read me. But I'm not homosexual. I like to wear dresses but I'm strictly heterosexual and have no desire to have sex with a man. I tolerated kisses because it is a necessary part of appearing to be a woman but I don't really get any pleasure from them."

"All right then, tolerate one more just for me." Then he pulled me close again and kissed me. He ran his tongue around my lips and then into my mouth. Then he kissed my neck and ear. I felt chill bumps when he did that. This time I felt his hand on my leg but it stayed on my thigh and didn't move upwards.

"See, that kiss wasn't too bad, was it?"

"It's time we go into the hotel, Mark." I scooted away from him and opened the car door. He scrambled out of his door and hurried around the car to hold the door for me.

As we started toward the hotel entrance he took my hand and said, "Your secret is safe with me. I would never betray a friend. You have showed me that some of the best are not on the stage. You can meet them in everyday life."

I looked up at him and smiled. "Thank you. I appreciate that."

"What does Clint know about you?"

"I have known Clint since we were in middle school together. I would die if he knew who I am."

"What about Ann and her mother? I assume they know about you."

"Oh, yes," I giggled. "They have known about me since I was in grade school."

We entered the lobby still hand in hand and walked to the elevators. At the door of my room I turned and looked up at Mark. He looked down at me and smiled. Then he put his arms around me and pulled me close. I looked up and our lips met for one last tender kiss. Then I said, "Thank you for a truly wonderful evening." I turned and slipped inside the room.

I undressed and slipped on a white baby doll pajama. Then I removed my wig and cleaned off my makeup and moisturized my face. I was propped up in bed reading a magazine when Renee came in.

She began to undress and interrogate me. What was Mark so secretive about? Even Clint didn't know where you were going? Where had you gone? What did you do? Why was I back so early? I tried to avoid her questions but she was relentless. Finally, I gave in and told her the truth. "Mark read me. But the funny thing is that he said he was jealous of me because I could pass in public and he could not. But because he likes to dress up he was more observant of little things that tipped him off. He wasn't mad. And he didn't stop treating me like a woman. He was very nice about it all."

"Well Clint sure was all hands tonight. He wasn't as rough as Harold or Wally but he made a good effort to get in my pants."

By then she had finished undressing and removing her makeup. She slipped on a gown and climbed into bed beside me. "I finally told him, 'I'm not that kind of girl.' But I am this kind of girl." With that she pulled me to her and kissed me on the mouth. Our tongues met as my hands began to explore her body.

Sunday morning we dressed for travel. I decided to wear a white suit with a mini-skirt and jacket that came to within a couple of inches of the hem of the skirt. I put on white panties, a white padded panty, nude very sheer pantyhose and a white bra. The skirt was lined so that I didn't have to wear a slip but I did choose a white cami to wear under the sheer white blouse. I carefully applied my makeup - foundation, powder, blush, eye shadow, eye liner, mascara and lipstick. Then I put on the blouse and skirt and seated the wig on my head. Finally I slipped on the jacket and a pair of white sandals with 4 inch heels.

We packed and after breakfast made our way to the airport where we met the others from our office. Fortunately, our schedule didn't coincide with Clint and Mark. That might have made some complications. The flight home was uneventful.


Chapter 11

Back to "Normal"


On Monday things were pretty much back to normal at the office although there was a lot of chatter about which shows each one had seen and what they thought about Las Vegas with video poker and slot machines everywhere. By Tuesday we were settled back into routine.

I let a week pass while I planned and stewed and planned again my next course of action. Friday evening I went directly home from work, picked up the bag I had packed and drove to Mother's house. I called her only as I was ready to leave the apartment. I didn't want Ann involved in this visit. She would surely complicate things.

It was already getting dark when I arrived. I pulled around back and parked in Carl's usual space. At the kitchen door I called "Mother" and walked in. Mother turned off the television as she got up from her chair. She met me in the kitchen with a hug and a kiss on the cheek.

"I'm glad you came," she said. "I've been worrying about you."

"Oh, I'm all right, I guess. I just need some wise counsel and you're the best at that of anyone I know." Mother smiled.

"Would you like a glass of tea? Supper will be ready in about 20 minutes. I assume you haven't eaten yet."

"No, I haven't eaten and yes, thank you, I would like the tea."

I watched as mother stirred batter and poured it into a pan and put it in the already hot oven. Then she took a pitcher from the refrigerator, put some ice in two glasses and a squirt of lemon concentrate in each and poured tea. We sat in the den and looked at each other for a long time before I started to speak.

"Monday I plan to talk to Ellen. And I may be out of a job before the day is over. May I come home if necessary?"

"Of course you can, Honey. You know you are always welcome here. You are my child." Mother is not only wise. She is a diplomat. She had said, 'my child' not 'my son' or 'my daughter.' She wasn't making any assumptions about what I would do nor pressuring me one way or another.

We moved to the table and she served hot cornbread and black-eyed peas, one of my favorite dishes. "Humm, that looks delicious."

"I though you would like it so when you called I got ready."

During dinner we talked about her garden and how wet the weather had been lately. She caught me up on all the family news and much of the local news.

After dinner I put on an apron and washed the few dishes as she cleared the table. Then we went to the den and continued our conversation.

We talked at length about my options and the possible results of each. When we had pretty well worked that out we moved on to other things. I told her about the convention and seeing Mark and Clint there.

She said that she had run into Mark at the supermarket and he had mentioned seeing me in Las Vegas. He said that we had a good time together.

As bedtime drew near, Mother suggested, "Why don't you sleep in Ann's room tonight. That way you will have a dresser to do your makeup in the morning."

Saturday morning I decided to just relax and enjoy being home. I dressed in a jeans mini-skirt and a white short sleeved tee shirt with a kitten embroidered on the front. I stepped into a pair of flats and put on minimal makeup and the wig and went to breakfast. Mother smiled when she saw me.

"Do you really like being a girl?"

"Sometimes I love it. Sometimes I hate it. And a lot of the time it is just clothes, not any different than when I wear boy's clothes."

The rest of the morning we talked about work and the people I worked with. We talked about what might be their reactions if I went back to being a boy. But in the end Mother said, "Honey, it is your decision. You know the people. You know your feelings. And you will just have to make a decision and then live with the consequences."

I nodded and dropped the subject.

Saturday afternoon I drove back to the city with my mind made up.

On Monday I went by Ellen's office and said, "Ellen, would you go to dinner with me this evening?"

She looked at me and grinned. "Are you asking me for a date?"

I grinned back at her and said, "I have thought about that but this is to talk business unless you want to make it a date afterwards. I wouldn't be opposed to that."

"OK, I'll go."

"Thanks. I'll pick you up about 6 pm. Do you have some place special that you like to eat?"


"How about that new Chinese place that just opened on the Southside?"

"That sounds good to me."

After work I went home and laid out the most feminine outfit I had, the Georgette print dress. I bathed and dressed in black panties, padded panty, nude pantyhose, black bra with wide set straps that showed a lot of the top of my breasts and a black half slip. Then I did my makeup for evening, with more eye shadow, eye liner, mascara, and lip liner and lipstick. I pulled the dress over my head and worked the zipper up the back. Then I settled the wig on my head and fastened it down. I chose black sandals with 4 inch heels.

When I arrived at Ellen's apartment she was ready, dressed in a black dress that had a fitted bodice and an A line skirt.

As we ate I purposefully avoided the reason for our meeting. We chatted about work and the convention. Ellen was pleased with the way things had gone. She had gotten good reports from others on my participation. Finally, as we returned to the table with our desserts she said, "All right, out with it. What is on your mind?"

I reached across the table and took her hand in mine and looked her straight in the eyes. "I confess to really mixed emotions in this. I appreciate the opportunity you have given me to explore my feminine side and to do what I have always wanted to do, live as a woman. But the truth is, I am not a woman. I have no interest in becoming one. And I am not homosexual. I love the clothes. I love to dress up. I don't even mind doing all the things that a woman has to do to get ready to go to work or to go out. Although I admit, it is a lot easier being a boy. But the fact is that I am ready to end this little charade."

"I was afraid that was what this was all about. Renee told me that you were not excited about dating and especially about being kissed by men. She did say, however, that you seemed to get along better with your friend Mark. So what do you propose to do?"

"Mark is a special case. Please don't tell anyone but he is a closet transvestite. He confessed to me the last night we were in Vegas. So he's different. But still, that doesn't count.

Did Renee also tell you that she seemed to take special pleasure in 'confirming' my sexual orientation?"

Ellen's laugh was almost a snort when she heard that. "No, the little tart didn't tell me that part."

"You notice that I didn't say that I don't like working for you and the organization. I didn't say that I don't like the others in the office. I would just like to return to being a boy. But that isn't as easy as just taking off the dress and coming to work tomorrow in a coat and tie."

Ellen studied my face with its tweezered eyebrows. Then she looked at my fingers with their acrylic nails. "No, I suppose it really isn't that easy is it."

"If you will let me, I will start the transition back by letting my eyebrows and nails grow. In a couple of months or so my face would be able to make the transition back to male. The nails will take a little longer unless there is some solvent that will take them off. By then I will be due vacation time. I can go away as Cheryl and come back as Carl."

Ellen pursed her lips and thought about it a while. Then she said, "OK, we will move in that direction. But does that mean that Cheryl will be gone forever?"

"Well, I won't stop dressing up, if that is what you mean. I don't think I could stop no matter how hard I tried. But it will be more limited. Probably just weekends."

"Would Cheryl come back to work next year in time for the convention and maybe some other times if we needed her?"

"I hadn't thought about that but I suppose so, if it were for the good of the team. I owe you too much to refuse that."

"Honey, I don't want you to do anything because you feel a debt to me. I've just enjoyed having Cheryl around. She fits so well into the team and I hate to loose her."

We finished our desserts in silence. I paid the check and we left the restaurant. As we walked toward the car Ellen said, "I know a club where it isn't a scandal for two women to dance together. Would you like to go there and dance a while?"

I smiled at her and said, "If you will lead. I had never danced much until Liz taught me and she didn't teach me to lead."

"OK, I can lead."

We walked into the club past a bouncer who, although obviously female, looked like she could have played tackle for the Atlanta Falcons. As we entered Ellen took my hand. "To keep you from running," she said. The room was mostly deserted. Most of the women were in pants of one sort or another - jeans or slacks with a few in Bermudas. Some were made up and some were not. Three or four couples were on the dance floor swaying to a slow song.

We were shown to a table and sat down. Ellen asked what I would like to drink. I said, "Just a coke or something like that."

"OK, then. Tonight is non-alcoholic. It's a sober occasion."

I smiled at her and said, "I hope it isn't too sober."

We took a few sips of our drinks then Ellen said, "Let's dance."

The music was soft and slow. We moved to the floor and she led. Our breast collided. After we had danced a few minutes she said, "You dance very well. You will have to learn to lead."

"Maybe I will ask Liz to teach me that."

"Well, I could teach you. Unless you are afraid of the boss, that is."

"Is that an offer?"

"You can take it that way if you want."

"I think I like that offer," I said. And then I kissed her on the lips. It wasn't a hard kiss and didn't linger. I sensed her surprise but also sensed an immediate response.

"My, you may not like being kissed by men but you certainly seem to have a way with women."

"Not really. That was just an impulse." But I kissed her again. This time I lingered more and felt her return the kiss. The music ended and we walked off the floor hand in hand.

We danced and talked for a while and then Ellen said, "Tomorrow is as work day. We had better head home and get some rest."

We left the club and walked hand in hand to the car where I opened the door for her. "My, even in a dress, you are the gentleman."

"That has been a hard habit to break."

At her apartment she leaned across and kissed me quickly on the lips and then opened the door and scooted out. She leaned down and said, "I'll see you tomorrow." And with that she closed the door, turned and moved quickly toward the building.




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