Crystal's StorySite

This is story about how a male transvestite captured and won the heart of woman. No explicit domination. Voluntary cross dressing.


My Life With Shirley

by Amelia Allyrw


Let me introduce and then I will tell you my story. My name is Anne Macdonald. I am a legal person, a lawyer. I am twenty-seven years old and have my own office and a rising number of clients. No, I do not represent any of the major financial movers and shakers, but I do have a number of small clients who run their own business. In the main, they consist of real estate operators and operators small businesses whose problems consist largely of. Handling legal requirements for commercial transactions and taxes.

No, I do not solve dramatic murder cases like those movie lawyers who never have to worry about their client's finances or receiving fees. Most of my work consist of verifying business transactions and arbitrating differences in contracts or legal questions, sometimes to the point of going to court.

Now, I'll tell you my story. It began with a meeting with Simone Dubois regarding the consignment of some exclusive gowns. Simone is the owner and operator of "Simone's Exclusive"'. This was a boutique selling dresses and other women's wear. She handles exclusive, lady's clothing. These are the kind that cost upwards of several hundred, sometimes thousands of dollars. Those are her gravy sales, and she gets plenty. Her bread and butter income consists of sales of the more popular priced garments. Women come in to ogle and drool over the expensive creations, then buy dresses in the fifty to a hundred dollar range. It is popular store, well known, with no lack of customers.

I met Shirle as result of one of my meetings with Simone concerning settlement of liabilities for some expensive gowns she was handling. She had to furnish documentation regarding potential loses due to theft, fire or any other disasters.

It seemed to be more or less the standard requirements of the manufacturer for protecting his goods. A quick review indicted that it was more or less a standard requirement and she should have no problem with her current insurance coverage. There were a few clauses that I suggested that she get an agreement on, but nothing that would trouble the transaction.

After the business was done in one of these cases, we would spend a few moments discussing things in general and then she asked me if I could help one of her employees obtaining a legal name change. I explained what was required and suggested that the person come in the next day with the documentation.

The next day, about nine A.M., a woman came by, saying that Madam had recommended me for the task of getting a name change. She was an attractive woman about five-seven. She had startling blue eyes, and her hair was dark, almost auburn, prepared in a page boy style. Her mouth was a bit wide, but that actually enhanced her appearance when she smiled and showed off her perfect teeth. She was a bit nervous and appeared kind of reserved, but had a winning smile and projected a shy but kind of pixiesh attitude. She wearing a conservative black knee length dress with a large white collar. The dress was discreetly open at the neck, showing a necklace with a small gold pendant. Her shoes were flat with a one-inch heel. When she saw me looking at them she explained that while standing all day, demonstrating merchandise, she wore the most comfortable shoes she could find and still look stylish.

In looking over her papers, I noted that she wanted her name changed from Sheldon Anders to Shirley Anders. When I asked her for the reason for the name change, she explained, "I'm tired of receiving invitations for credit cards and other promotions addressed to Mr. Sheldon Anders. If I make appointments, often time I am listed as Mr. Sheldon Anders and receive odd looks and some times outright insults when I show up wearing a dress. I elected to live and appear as a woman and don't want to have to go through life explaining that I prefer Miss, or Ms instead of Mr..

I explained that I could get the name changed but legally she would be still belabeled a man.

"I don't hide the fact that I am a man, but at the same time, I don't intend to advertise it. I just want my credit cards and other identification with the name "Shirley Anders".

I replied that I understood her problem and could see no real problem getting the name changed would not change the data in her birth certificate and that she would be labeled as a male in legal documents.

Once that was settled, we spent a few moments in general conversation. I mentioned that I was amazed of her appearance and asked her if she had any physical or facial modifications to emphasize her feminine appearance.

She laughed. "No this is me. I'm amazed that I still look OK. When I was growing up there were plenty of boys (and even a few men) taking exception to my face, calling me a sissy or fag or other derogatory expressions and more than once I had to go to fist city. Thankfully I won most of these encounters and did not receive any permanent disfigurations.

"No, in answer to my query. I have no intention to having any sex change. I guess I'm unusual but in spite of my love of feminine clothing and life style, women still look sexy and attractive to me. Maybe I'm so entranced with them that I want to emulate them"

With that, Shirley excused herself, saying that the store opened at ten and the Madam expected the employees to be there about nine thirt. If she hurried, she would meet the deadline.

When she left, I spent a few moments thinking about her. She intrigued me. For a male, she was the most beautiful woman I had ever met, and I met a lot of them in both in my business and social life.

But what caused her to emulate a woman? How and when did she decided to adopt a female gender? What was her family life like and did they approve of her cross-dressing. She mentioned that she was sexually interested in women not men. How often did she experience sex and did she find it easy to find women that were interested in her in a sexual way? Why was I so interested in her; or him?

A few days later I mentioned to Simone that I had met her employee. Then asked, almost piqued, why she did not reveal her true sex.

Simone laughed, "I thought you needed a bit of a surprise. "You are so sure of your ability to analyze people that I wanted to see if you could read her. But I'm not surprised that you missed.

"I met Shirley months ago. She was a waitress in a restaurant I used to attend. One day while she was serving me, I asked why she was imitating a woman. She seemed surprised but not upset and wanted how I was able to read her actual sex. saying that she had been living this way for well over a year and this was the first time she had been challenged".

. "I told her I was in the women's apparel business for over twenty years and had had met women of with sorts of mannerisms and habits and it was quite easy to be able to notice slight unladylike manners in males trying to pass as women".

"We then talked for a few moments and when I asked her if she wanted a job in my store doing various and sundry tasks in the backroom. She would be doing what was necessary to get merchandise ready for display or removal. Also she would work with two employees that would give her pointers on proper feminine behavior plus anything else that needed to be done. I added that if she proved capable that eventually she would get a raise and go on the floor as saleslady".

"She accepted without even asking her salary. She said that she was always interested in clothing design and this seemed like a wonderful opportunity to get experience, and that she would appreciate any help she could get improving her feminine style.

"She has been with me for almost two years now. Shortly after I hired her, one of the sales ladies had called in sick just at a time when we were quite busy. With a bit of trepidation I asked her to fill in. I had experienced problems with some of the more snobby customers that wanted perfect service and would be upset and angry for the slightest deviance in the saleslady's proper attitude toward them. Shirley worked out perfectly, in fact I received compliments on having such wonderful employees".


A few days later I called Shirley saying that her application was being acted upon and she should be in court the next day at Three PM. A few minutes, before three, we met in front of the courthouse and entered. The interior of the place was no better than it's outsides aged appearance. Dingy would best describe it. The interior looked like it was in desperate need of refurbishing. The courtroom was run down, dark and obviously relegated to minor cases such as building permits and of course, name changing and any other minor problems not necessarily of a criminal matter. A few cases were still ahead on the docket, such as obtaining permissions to do some reconstruction

At the judge's order, we approached the bench. The judge, who looked like he should have been retired twenty years ago. In spite of his aged condition, he was alert and strictly business. He began asking her questions; had she brought her birth certificate? "Yes". Why did she want her name changed? "To match my chosen life style". The questions and answers rattled on. They were all routine. No criminal record. no open charges. No bills, no this, yes that. Finally the questions ended and with his signature, the name change was legalized. With a flourish he handed the document saying, "You are now. named MISTER Shirley Anders". Accenting the mister..

By the time it was over, it was rather late and I offered to drive her home. When we arrived, she asked what I was going to do,

Not much, I replied, "grab a bite to eat and go home and go over a bunch of cases that were pending and must be reviewed"

She asked me if I wanted potluck with her. She said that she had made up some spaghetti sauce and there was plenty for both of us. Without much resistance, I agreed.

The meal was delicious, including the fine wine she served with it. She then produced a German chocolate cake that she had baked yesterday.

"Since I'm living as a woman, I should be able to perform the arts that traditionally considered female. Cooking among them, besides I enjoy doing it". She replied in answer to my query.

When we completed our meal, I fell on the couch exclaiming I was full and thanked her for the delicious meal. When she cleaned up, she sat beside me poring out the rest of the wine.

It was then when I asked her how come she decided to live like a woman.

"It's a long story and if you want to take time to listen, I'll give you my life history"

"Go ahead, I'm interested". I replied, "The briefs can wait".


Shirley's story

"I guess it really started when my father died, I was about five at the time. My mother used to take delight in occasionally dressing me n a girlish style and try to teach me to sew or knit. I thought it was fun. Afterward, Dad would take me outside and we would play ball together, or pass a football. And that was fun".

"When. Dad died, We didn't have any relatives that lived close by so Mother became more possessive over me than ever. She didn't know any sports, so she taught me to sew and embroider. She also taught me to cook and even bake cakes. It pleased her when I embroidered some napkins or baked a cake. It was about that time that I got interested in women's clothes, I would sneak some of mother's clothe and try them on in the privacy of my bedroom. I am sure she knew about it but never mentioned it".

"Then things got different. Dad didn't leave us much money and we had no close relatives nearby so when she met Mister Mudge, she was entrance by his polite and gentle manner. He was rather wealthy and was influent in the community. I guess he convinced her she needed some one who would love to take care of her and that I needed a male authority figure to teach me how to be a man".

"When she married Mister Mudge, things changed, He treated mother OK. But seemed to resent mother paying attention to me. He and I did not get as long as well. He had definite ideas as to how I should act and had no use for Mother teaching me "girly" things. He also seemed to think that mother dressed me in "sissy" clothes. Now they were strictly boy's clothes but in bright colors. He seemed to think that they should have been all black or at least, dark".

"I still would occasionally "borrow" some of Mom's clothes and try them on in the privacy of my room. One day he caught me and had a fit. "I won't have any Homosexuals in my house". He roared and beat me with his belt. As I lay on the bed, sobbing in pain, he shouted. "If I ever do something like that again, you will sorry".

"He yelled at mother who had heard the shouting and came to the room to see the cause. Seeing mother, he shouted at her, "Your son has been wearing your clothes and prancing around like some queer. If I ever see him in those clothes again, he'll get worse than what I just did. I hold you responsible that he doesn't do that again".

"Wen they left me alone and sobbing, I thought how I would get even with him. I would finish high school as I wanted to get my education, but after that I would leave home and wear women's clothes all the time. I would live like a girl".

"If it wasn't for the home life, high school would have been enjoyable. I made the baseball team playing second base and also made the Tennis team. Being as small as I was, they wouldn't think of accepting me to try out for football. I had a few dates and even went all the way a couple of times. I must admit that the first time was a disaster. I got excited and soiled my pants. Actually, in spite of making the athletic team I didn't do to well with girls. I was quite shy and I guess they thought I was to small for them. It made the uncomfortable, and let it show.


"L also watched girls, not so much for their attractiveness (which I did) but I wanted to learn their feminine actions and manners so I would act more natural as a girl".

"I worked after school and week-ends to get some funds to get me started. We won't go into details about how I managed the first few months of my independence, but it was touch and go. What I thought I had plenty of funds to get m started, I was woefully understated. Just to rent a room cost me almost a third of my stake. I had to delay buying many feminine clothes until after I found a job which I found was not to plentiful for a person of my experience. Goodwell was my favorite boutique.

"I found out I could occasionally get by with my male blue jeans, shirt and tennis shoes plus a panty girdle to hide my genitals, especially if I let the shirt tail hang out. All I had to do was change the part in my hair, apply a bit of mascara, and eyebrow pencil along with a bit of pink gloss lipstick and I was lost among the rest of the teenage girls.

. I finally landed a job at a fast food restaurant. Later I got a better job as a waitress in a higher class restaurant and slowly built up a wardrobe of feminine clothes and started taking a couple of courses in drawing and dress designing. I must have done pretty well because no one challenged my sex, that is, until Madam Simone "read" me. She was cordial and listened to my story about how and why I chose to live as a girl".

"When I told her I my story and now I was taking courses in drawing and dress design in the evenings, she offered me a job in her establishment doing mostly clerical chores. She explained that most of the dresses she received were on consignment and records had to be kept of their sales and returns. Also inventories had to be kept on accessories, hose, underwear and things of that nature. She said that she had two other employees that would help me improve my feminine behavior and teach me the fine points of the clothing we handled. After about six months of training she allowed me to be one of the saleswomen". It as then I had my facial hair removed. Every time I got a few dollars ahead, I would have a bit more done. It took about year or so, but finally got red of my facial hair.

And here I am. Now how about you"?

"Nothing much about me". I replied. Mother and Dad were happy together and besides me, I had a sister and brother. After High School I went to college, got a degree in Law, passed the bar and after a short time working in law office, I went out on my own. I now do well and have my own office and a number of clients. No dramatic past as you experienced"


On the way home, I thought about how she managed to keep her optimistic outlook on her future and show such a pleasant and humorous attitude. And what's more, she could cook!

The next week, one of my clients gave me a couple of tickets to a play. It had received several rave accolades. Since I didn't have any close friends that would be interested in plays, I called Shirley and asked her if she would like to go with me, (I'll be honest; Shirley was my first and only thought). She sounded delighted and quickly agreed.

That evening when I came by to pick her up, I was amazed. Here was the loveliest woman I ever saw. I had thought of myself as attractive, but this person eclipsed me. She was perfectly made up, her eyebrows were arched and she had the proper amount of eye shadow. The eyelashes were well defined and gave her eyes a sort of mysterious appearance. Her auburn hair draped in smooth waves down her shoulders length hair She was wearing a form fitting long red dress, sleeveless, modestly showing a bit of skin about the shoulders. The skirt had slits on each side, starting from just above her knees, to the hem, allowing her to walk; slink would be a better word. She had red shoes with three -inch heels and matching red purse. She was wearing a pearl necklace and bracelet. They may have been faux, but they did top off the ensemble. When I complimented her on her outfit, she said with a smile, "Every now and then we get a dress that was not sold and the manufacturer does not particularly want it back, so we can buy it for pennies on the dollar".

Now I had thought I was quite good looking but she eclipsed me. In fact, when we arrived at the theater, she eclipsed everyone, women that is. The men would just gawk. At one time she whispered to me. "What is the matter with me causing all those people to stare at me"? I told her to forget it, the women were envious and she raised the libido of all the men.

The dinner and play was a huge success. After the play. I asked her if she would like to come to my apartment and have a nightcap. She hesitated a moment and agreed so we found ourselves on my couch after I had prepared a couple of stiff drinks. Well one thing happened after another and we found ourselves stripped for action ready for bed. I noted that he hade to wear falsies, He mentioned that she would consider implants when He could afford them. His breasts though not enlarged, had nipples that were more pronounced than a normal male, his hips were more rounded and his body was smooth with no sign of the knotty tendons common in men. (Please note that I try to refer to Shirley as she when she is wearing feminine attire and a he, unclothed).

When I commented on his body's attractive appearance, he said that Ms. Simone had introduced him to a Gynecologist who had wrote a prescription for some female hormones and telling him it would partially smooth and round out his body's appearance. The doctor had said it was a low dosage hormone and should not have any effect on his sex life. Later if he wanted higher doses to emphasize his curves and even grow breasts, ithe effect of the femine hormones, they could be temporarily counteracted by those male sex pills that promote erection and are so popular and widely advertised.

I quickly found out that once we were stripped he was all male. We kissed as we crawled into bed. the kisses quickly got more erotic and we were searching for new places to put our mouths. He was busy on my breasts when I gently pushed his head downward, he took the hint and without hesitation his mouth became busy exploring my intimate feminine apertures. When I began to writhe in excitement, he quickly changed position an inserted his manhood in the cavity that was well lubricated with his saliva,

He immediately began thrusting; I answered thrust for thrust. We enjoyed ecstasy forever, which lasted all of fifteen minutes. His semen began ejaculating and I responded, absorbing every drop. (Later I hoped that my pills were working.).

It was all to soon that we both began to relax and come down from our exalted state of emotion. My breath began to slow and my body relaxes while snuggling against his body, damp with perspiration.

"I love you!" He whispered. I answered his kiss. For the moment my mind was in such turmoil, I responded. "I think I love you too. But one night is not forever. Let us wait a bit before we make any commitments"'

"I understand". He answered, "It's just been so long and that except for you and Ms. Simone no one has ever acted kindly to me since I struck out on my own, I guess I overly acted. But I still love you".

We experienced intimacy twice more that evening and it seemed like each one was better that the last. Each time I could feel my resolve not to get overly involved with him grew weaker.

The next morning we took a shower together and got our last chance at fondling each other. After donning her slip and brushing out her hair she donned the dress she wore the night before and I must say she looked as well in daylight s she did last evening.

Was it possible I could fall in love with a person that was half girl? It seemed the possibility grew better with each moment of companionship.

As I drove her home, I mentioned that it would be nice to get together again. She replied that it would be wonderful but said that she could not afford a play and expensive but we could go to a movie and she could fix a supper.

I could live with that and answered that while I am pretty busy on evenings working on various briefs or other legal matters, I kept myself free for the weekend. She asked and I responded that we could get together next weekend.

All the rest of the week, my mind was filled with thoughts of Shirley. Would I want to live with her? What would people say and would it have any effect on my business? How would it be to live permanently with another woman? Not having an answer, I decided I could wait and enjoy the relationship.

The next few weeks we spent each weekend together, Sometimes we would spend the night at my place, sometimes hers. Occasionally, I would find a few moments during the week and meet her for lunch As the weeks passed I found myself enjoying just being with her/him. I no longer thought of him/her in terms of gender. This was a PERSON that I enjoyed being with. I was finding my self slowly finding myself in love with the whole individual. (Well, maybe not so slowly.) As a woman, she was enjoyable company with her warm personality and delightful sense of humor that made her a wonderful companion in exploring new places and trying new sensations. The fact that she was an excellent cook only affirmed my feelings. At the same time I enjoyed him as a handsome lover, gentle and compliant to my every wish.

One day she mentioned that her lease would soon be up. The building was going through some renovations; she would have to move. Without hesitation I asked her to move in with me. She demurred saying that no way could she afford even half of the rent on my condominium. We argued about it, but when I convinced her that with or without her, there would be no change in my payments. After an extended period, she agreed that she would pay the same as her current rental charges. I think the move was to my advantage. Not only would I have someone to keep me warm at night, but I now had an excellent cook that enjoyed preparing new culinary surprises.

We had occasional disagreements. She had a tendency to be more neat or fussy about keeping up the apartment. I don't say I was a slob, but leaving things laying about was no problem. We also had occasional spats watching TV. She occasionally liked action type movies, while I preferred more dramas. (I guess this action business reflected her masculine side.). Taking everything in consideration, we enjoyed each other's company and as time went on, our mutual feelings of affection only increased.

I'm not quite sure who brought up the subject, but having children came up. I mentioned that I wouldn't mind having a kid or two about the house and Shirley seemed enthusiastic about the subject.

A few days later, while we were cuddling in bed, Shirley proposed. It was about time, I thought. If she didn't I would have to. Somewhere in this relationship, tradition should be followed at least once. It was only right and proper that a man should be the initiator, even if he was wearing a fancy nightgown.

Once the idea of marriage was agreed on, the subject went from idle discussion to serious consideration. I mentioned that when, and if, we had children, we would have to hire someone to care for any children. Shirley quickly negated the idea, "If we have any children, I will be the caregiver". She would stay home while. I would keep my law practice. . She said that she had been receiving favorable reviews of sketches she had made of some of her of dress designs, and had already sold one " I could do the designing and drawing at home in my spare time". Well that settled that".

Once the decision had been made, when will this event occur? In full agreement we decided the sooner the better. There would be no ceremony or guests, well. maybe Madame Simone.

The next day we made our way down to the County seat to file for our marriage license. We dressed up for occasion. I wore a skirt, blouse combination. The skirt was knee length of red double weight cotton that draped gracefully. The blouse was ivory polyester with flowing sleeves and "V" collar. I had donned a gold necklace and a set of matching earrings. I wore sheer silk hose and two inch red shoes with a red purse to match the skirt. Shirley was wearing a knee length dress of light blue linen with a self belt and a full skirt that flared out enticingly as she walked. She wore a set of matching earrings and a necklace of brilliant red. She was wearing white shoes with a two-inch heel. She had a white linen purse slung over her shoulder. She never looked lovelier.

W approached the desk where a man was sitting. our heels clicking overly loud leaving echos in cavernous building. He looked to be in his forties with thinning hair and a bald spot showing through. "What can I do for you ladies"? He said with an ingratiating smile. His voice was kind of high pitched and had a semi drawl.

"We wish to get married". I responded.

He looked at as if we were a new species, and said. "A'hm sorry ladies but in this state we do not allow same sex marriages like they do in some of those other "Godless" states. He then added with a grin. "You know, you will have to produce your birth certificates as proof of age and sex".

We then produced our certificates and handed them to him. He began scanning them. Either he was a very slow reader, or was looking at every word and comma. He handed mine back and looked t Shirley. "This shows you as Shelton Anders and a male. Is that correct"?

After Shirley's confirmation he looked at the certificate, looking at both sides. "I do'no, this looks like it could be a forgery. I hear tales about how you .folks will do anything just to pretend that you are normal. If we could make a quick physical inspection, that will settle the problem". He said with a dare in his voice.

I replied, "The law states the a birth certificate, or other evidence be produced to show proof of eligibility. You have a copy of the birth certificate sex in your hands showing that we are of legal and is according to law". Nothing in the law states that a physical inspection is necessary. I will not allow my husband-to-be a subject of your prurient interests unless you can prove that is standrd procedure for every male to expose himself in front of you.."

I ain't got any "purient", or whatever, interests. All he got to do is prove to me that he is a man. Otherwise I will not issue you no license." With these words, he handed us our certificates and walked away.

I quickly filed protest, claiming discrimination and illegal conduct, demanding our civil rights

The next morning we returned to the courthouse, this time instead of facing n interviewer, we were facing a judge in a courtroom. We were both wearing similar knee length dresses of white nylon. These had been designed by Shirley for the marriage ceremony. High collars and long sleeves with ruffled lace on the cuffs. Ir had rows of lace covering the breasts. Our heads were covered with white lace that reached down to the nape of the neck. They gave an impression of innocence . These were prepared by a dress designer in exchange for the design rights

. The courtroom was just as shoddy and run down as the Marriage License office. The judge sat behind an elevated desk, (bench) and rapped the courtroom to order with is gavel. We sat at the lawyer's desk, which was nothing more that a table with folding chairs.

I arose and stated that our civil rights were being violated because after submitting data required by law we were being refused a marriage license.


The judge, a bit older and more intelligent appearing than the clerk, said, "I read the brief and the clerk states that he thinks the birth certificate was illegal and as such refused a license. He claims that he believes that you both are the same sex". H looked at Shirley, saying, "Are you sure that you are a male and the certificate was forged?"

"Yes your honor, I was born a male and still am. It's just that I prefer to wear clothes traditionally considered to be female".

"Well, we can prove your claim with a simple examination". When I started to protest, he refused; stating it was the duty of the court to resolve the matter, ordering Shirley to accompany him to his chambers.

The examination took only a few moments and as Shirley returned to her seat, the judge announced that the subject was a male and the license is granted.

He sat back, with a look of satisfaction, proud of his ability to settle a claim quickly.

I then asked, "Judge, since the matter is settled and you are legally qualified, would you perform the ceremony right here and now"?

The judge, still proud of his ability to settle a case, quickly agreed.

In just a few moments, we were legally man and wife. He handed me the license and stated, It is made out as you requested. I looked and saw the names were listed as Mrs. Anne Macdonald and Ms Shirley Macdonald, nee Anders. Iif you wish we can easily change the Ms to Mr". "Oh no!" Exclaimed Shirley, "leave it as it is".

After the ceremony, I asked the judge, "Your Honor, we went through a lot of trouble to prove Shirley's sex. How come that my sex wasn't questioned"?

The question wasn't answered as the judge realized that without any questions, no one had challenged my sex. Perhaps the license clerk had challenged the wrong person., he made a mistake and challenged the wrong person. The look of astonishment and doubt on his face was worth the entire procedure.

And so we lived happily ever after, -- Until the baby came.




2005 by Amelia Allyrw. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.