Mistress Psyche's Feminization Fantasies


Sissy Girl Stories


Take a Letter

By Nina

I had just graduated from high school. The year was 1939, during the great depression. The prospects of finding a job were very slim. I had no skills. I was/am of slight build so heavy construction or factory jobs were not for me. I had taken several courses in, of all things, stenography. In school and at home I was continually ridiculed for my choice but I just wasn’t the math or shop class type. I sat at home during the summer following graduation reading the morning paper want ad sections and practicing typing. One morning an obscure little ad caught my eye. It read, “Young person wanted for secretarial position to assist in managing large estate. Live-in required. Call----------.” It sounded like something I could do even though it seemed more like a girl’s job. I hastened to a local pay phone (we had no home phone- no money). A pleasant sounding older lady answered. She was not concerned that I was a male. Within minutes an appointment was set up for the next morning.

I followed her instructions, taking the Evanston “L” to the end of the line. I had to walk about a mile to her home in Wilmette. It was beautiful; huge grounds right on the lakefront. The house itself, more correctly a mansion, was the size of a hotel. My heart was beating a mile-a-minute as I rang the bell. A pretty young maid, quite tall, answered the door. I was taken aback. She wore a short, for that time period, black dress and high heels. Her waist was very small. Corsets were still worn ocassionally and she obviously was a devotee. I was greeted by name; a good sign I thought. When I regained my composure after seeing this lovely girl, I muttered a greeting. See escorted me to a small room that had been made into an office. There I was introduced to Mrs. Joyce Hamilton, the owner and my prospective employer. “So you are the young man I spoke to yesterday. Please stand away and let me look you over.” I stepped back a few paces. She eyed me from head to toe repeatedly. “You fill the bill physically, let’s review your qualifications.” As I went over my school training I wondered what she meant by the ‘physical’ comment.

When we finished she indicated that I would be satisfactory as she proceeded to outline my duties and responsibilities. I was to be her personal secretary and bookkeeper for the estate. She offered an exceptional salary, particularly for the period. She continued, “Before you except there is one thing you must know and agree to. I am a younger widow with a reputation to maintain. I cannot tolerate a hint of scandal to my reputation. I usually require all of my household associates to appear feminine. I am willing to make an exception in your case with one condition. You must agree to assume the identity of a female during your employment. That includes traveling to and from my home. What you do in your private life and in your home is your business but you must appear as a female at all other times”. I was dumbfounded. It seemed like she was asking a lot of me. Yet the salary was generous and jobs were scarce. She gave me a few minutes to think it through. I had a flashback to my early childhood. I remembered my mother dressing me as a girl for punishment. I vaguely recalled enjoying the episode. A further recall brought back a memory of being laced into a corset. Since the memory wasn’t repugnant I thought the offer might not be too difficult to accept.

The only drawback would be the ridicule at home. I would have to dress before I left for work and wear the clothes until I returned home. This would only happen one day a week, on my day off, since I would be staying here the rest of the week. It was as though she read my thoughts as she said, “Of course, if you wish you can stay here full time and avoid any embarrassment while traveling”. Then she added, “The young lady who received you is also a male. He uses the name Grace. What will your choice be?” Without thinking I blurted out, “Francine (my given name was Frank)”. I had just tacitly accepted the position. “Very well young man, I shall expect you bright and early tomorrow morning. Oh, and don’t bring any male clothes other than those on your back. As we agreed, you won’t need them and your new ones will be provided.” With that exchange Grace escorted me out. As we walked to the door she introduced herself formally and commented, “Mrs. Hamilton is wonderful and you will soon get used to your new clothes. I had misgivings two years ago but now they have become a way of life for me. Being a girl is so much more interesting and the clothes have an almost fatal fascination.” I was to learn she was so right.

My parents were elated. Of course I didn’t mention my prospective new clothes. Mom did question the matter of not packing anything to wear. I casually noted that the proper dress would be provided. Obviously I didn’t stress the word dress in my comment. I arrived at the Hamilton estate promptly at 8:30. I paid my morning respects to Mrs. Hamilton who then had Grace escort me to my room. It was very feminine in appearance, as I might have expected. It was rather large for a “servant” quarters and even had a private bath. In preparation my new wardrobe was laid out on the bed. The clothes were similar to Grace’s. I noted the dress was longer. With some trepidation I observed a very long corset. It appeared to be almost two feet long and generously reinforced with stays every couple of inches. Four garters were attached to each side. Lacing ran the full length of the back. I didn’t know if I could wear such a thing but it was part of the job I agreed to so I had little choice; no corset, no job. Besides, Grace seemed to manage in hers. It became obvious that Grace was to help me assume my new identity. “Take off those ugly boy things and let’s get you dressed, Francine.” I suggested that Fran would be fine. As I was aware that ‘she’ was a male I removed my clothes. Even so I was a bit red in the face from embarrassment. She did look like a pretty girl. As soon as I was naked she handed me a chemise. She then wrapped the corset around me and fastened the front hooks. I was covered from my armpits to my upper thighs. The lacing followed. Memories of my early “punishment” flooded back as the laces grew tighter and tighter. Breathing became labored. When the corset was fairly tight grace paused and reached down in the front of the corset. She gently worked the flesh on my chest upward and placed it into the bra cups. It’s not enough,” she commented, “but we will add some extra padding.” She then continued to lace the corset. I was obviously having a problem with the tightness. She paused again saying, “The laces are open three inches. I’ll leave them at that for a few days until you get used to the restriction, then I’ll close the laces. Madame insists that we girls have very trim waists. Within a few months you will have a waist like mine.” I took a closer look at Grace. I was going to look like that? Seeing the look on my face she said, “In case you are wondering, I’m laced to twenty inches. Of course it took two years to reach it and you will to.”

Still gasping for air, Grace rolled a pair of lovely tan silk hose on my legs, fastening them to the garters. The sensation of the silk on my legs was sensual. “Tomorrow we will have to shave your legs. These stockings are dark enough to hide your leg hair but lighter hose won’t”. I was then helped into a slip and a knee length pink dress. The dress clung to my corseted body. Grace then informed me that all my dresses would be custom fitted as my corsets were reduced. Shoes came next. “We’ll start with two-inch heels until you get the knack of walking in heels. Then you will gradually go up to five-inch heels,” Grace added as she slipped them on my feet. In spite of the tightness enveloping my waist I was beginning to find the corseted sensation pleasurable. What it might feel like at twenty inches remained to be seen. Makeup came next. Grace applied it rather heavily. A wig came next. “By this time next year you won’t be needing this,” she commented. I hadn’t thought about the long term. I had intended to take this position until I could find something more suitable for a male.

When she finished she led me to a full-length mirror. I was dumbfounded by what I saw. Frank had disappeared. A rather tall, slim-waisted girl stared back at me. Francine was born. If I had any trepidations about my job and what it entailed they disappeared with that vision. I suddenly felt as though this was something I had always wanted to do, perhaps destined to do might be more accurate. Perhaps Grace was right, I wouldn’t need the wig next year. I did like the new me. The only aspect to spoil the whole thing was my home life. My relatives would be horrified when I walked in. I would probably be disowned. I didn’t want that but if it happened, Mrs. Hamilton had indicated that I was welcome to stay seven days a week. I decided that I would not go home for a while until I could figure out how to break it to my parents. Grace then helped me get accustomed to my new footwear. I stumbled a lot at first but gradually learned to walk in them. Whether or not I would ever walk in four or five-inch heels was another matter. I would have to; it went with the position.

Since my parents couldn’t afford phone at home, Mrs. Hamilton graciously allowed her chauffeur, an apparent female, to drop of a note letting my parents know that I would be staying at her home full time for a while. If I couldn’t come up with a solution to my boy in dresses dilemma it might be for a very long time. She decided that I would spend my first day getting used to my new self. By evening I was becoming used to the tight-laced feeling and found it pleasant. Dressing as a girl didn’t seem like the worst thing in the world. Rather it almost seemed normal. I had heard stories about young boys, usually much younger than me, who were forced to dress as girls and resented or even fought it, understandably so. Yet here I was dressing more or less voluntarily and seemingly liking it. It was as though it was a renewal of my long forgotten childhood experience. I recalled an old saying, “As the twig is bent, so grows the tree.”

The next morning after bathing, Grace took a razor and shaved my legs, arms and armpits. “We can’t have unladylike hair can we?” she joked. Grace then proceeded to dress me. I was again laced into my corset, a bit tighter than yesterday but not uncomfortably so. Light colored hosiery were rolled up my legs. The feeling of the smooth silk on my shaved legs was even more sensuous than on my unshaven legs yesterday. I wore a lovely green silk dress, fashionably to my knees, with matching shoes. Grace explained that the servant girls all wore black, but I was a special employee and allowed, no required, to dress in the latest fashions. I couldn’t look like an ordinary servant. From time to time I would be required to meet with solicitors and business people. I hadn’t anticipated meeting strangers. The thought of having them accept me as a lady particularly thrilled me. A glance in the mirror assured me that they would never suspect my true identity. Unlike the staff, I was to take my meals with Mrs. Hamilton. I was now an elegant lady in elegant surroundings. The staff, except for Grace, were to address me as Miss Francine. I knew it wouldn’t be long before Frank would be a distant memory. I presumed that except for Grace, all the staff were female. Grace later informed me that all were males in women’s attire like us. Mrs. Hamilton must have had a secret reason. I was certainly not one to question it. She was wonderful to all of her staff, unlike many wealthy dowagers. The staff apparently didn’t mind their unusual dress situation nor did I.

Within two months I fully indoctrinated. I took care of paying bills, hiring contractors for repair work, supervising the staff, bookkeeping, keeping track of her appointments and any odds and ends that cropped up. Mrs. H was writing a novel and I did the typing and proofreading. My corset lacing was finally closed at twenty-two inches and I was promised a new, tighter one. I was so enthralled with my corset that, at Grace’s suggestion I slept in it. I could now navigate on four-inch heels. I hadn’t worn a stitch of male clothes since I signed on. Frank was rapidly becoming history. The holidays were approaching and I wanted to join my family for and old-fashioned Christmas, but how? I would have to appear at the door in female attire. Dad would have a fit. Mom would cry and carry on while my sister would laugh me out of the house. I finally had a long talk with Mrs. H. She was very sympathetic. She pointed out that all of her staff had the same problem and all survived. She added that I was still their only son and they loved me. She finally convinced me to go home on the next Sunday. She would have the chauffeur drive me home and wait for me. If it looked like I was accepted she would leave and pick me up on Monday.

Sunday I awoke as a nervous wreck. Grace helped me dress as usual. I wore a lovely knee length powder blue silk dress that was glove tight over my corset and matching shoes with five-inch heels. I hardly ate any breakfast. True to her word, her chauffeur was waiting for me. My legs shook as I walked to the motorcar. We finally pulled up in front of my home. I managed to stumble to the door and knocked. Dad answered and stared with awe at the pretty girl on his doorstep not realizing that I was his son. He finally asked, “May I help you?” I said, “I would like to see Mrs. Baxter (my mother).” Mom came to the door and invited me in. “I don’t believe we have met, how may I help you?” I answered, “Don’t you recognize me? We’ve met many times,” I replied, postponing the inevitable. Finally I blurted out, “I’m your son Frank.” Dad hit the ceiling, figuratively speaking. Mom burst into tears. After a few awkward minutes of nothing they demanded an explanation.

As I tried to explain dad kept muttering, “A fag, my son’s a fag.” It took at least an hour for them to settle down. I repeatedly assured dad I was not interested in boys (at that pointed I wasn’t sure myself). I further assured them that it was part of the job and I was actively looking for a position that would let me resume my masculine self (a lie). I told them I hated my feminine clothes (a lie) and couldn’t wait to get out of them. They finally grudgingly accepted my situation. They even went as far as to say that I made a very pretty and convincing girl. My sister surprised me. Instead of ridicule she hugged me and whispered, “Now I have the little sister I always wanted.”

The day passed quietly although I could feel the tension. If they had known that I had no intention of giving up my new life things would have been different. I had lied to them. I had no intention of giving up my corsets, heels and lovely clothes. We made plans for a holiday party. Dad made it known that I was expected to dress as his son. He would be disappointed. True to her word, the chauffeur picked me up the next morning. There were mixed emotions as we said our goodbyes. Mom said, “I don’t care what you are, I love you.” Sis said, “Come back soon baby sister.” Dad gave me a rough hug saying, “A corset is a hell of a thing for a boy to wear.” Mrs. H greeted me upon my return. “How did it go Fran?” “Better than I expected but not as good as it might have, “ I replied. She poured glasses of brandy and we had a long talk. I told her of my love for my new life and that I never wanted to return to my former existence. She assured me that I would have the position as long as I wanted and I would always be welcome to stay with her.

The holidays finally arrived. I was given a week off to visit home. My traveling wardrobe took up three large suitcases. My waist had been undergoing training in my new corsets, resulting in a twenty-inch waist. When the chauffeur dropped me off my homecoming was quiet but not very cordial. The first day dad kept ranting and raving about my clothes, the corset in particular. “No boy has a waist that small and why the hell do you like to wear it?” were among his comments. Mom cried at first feeling bad that she had lost her son but finally accepting her new daughter, “Temporarily” as she put it. My sister on the other hand seemed to still like the idea of having a new sister. She jokingly expressed envy at my “fabulous figure” as she put it. I later offered to bring her one of my old corsets. She declined, with a wistful look in her eyes saying, “Girls nowadays don’t wear them. I’d be the laughing stock of the office.” Except for occasional snide remarks from dad and a crying bout or two from mom the holiday was uneventful. As I left dad kissed me on the cheek saying, “I guess shaking hands with my daughter wouldn’t be acceptable.” Had dad given in and was accepting me? Only time would tell. With each passing day I became more enamored with my lifestyle. It was as if Frank never existed. I wisely limited my tight lacing to twenty inches. Anything smaller would have been impossible to hid under normal street wear.

 A month or so later Mrs. H’s personal maid fell sick. Mrs. H must have had a lot of faith or whatever in me because I was summoned to her bedroom, normally off limits. I learned that I had a new task until further notice. I was asked to lace her corsets and assist with her toilette in addition to my other duties. Mrs. H was not a young woman, perhaps close to forty-five. It seemed old to a young person my age. She was however lovely. Over the last year I had developed a secret crush on her. The idea of attending to her personal needs was more than I could have hoped for. My first morning I went to her room to tighten her laces. She had already wrapped the corset around her body. Her corset was much longer than mine, extending several inches over her thighs. I noticed that her garters were very short. I thought, “She must have to wear very short stockings with a corset that long.” I soon had her fully laced. Her waist was larger than mine but still very remarkable for an older lady. She sat down for me to fasten her stockings. As I fastened the garters I “happened” to look under her corset skirt. I was shocked. Mrs. H saw the shocked look on my face. “I’m surprised you didn’t know, but then the others were sworn to secrecy. Yes, I’m really Mr. Hamilton. I have been masquerading ever since my wife passed on twenty years ago. I expect you to let this go no further. I even assumed my wife’s name, Joyce. Since you are my most trusted employee you may use it when we are alone.” At first any comment I might have made was at best incoherent. Finally I swore to complete secrecy. Who was I to judge anyone considering my own situation?

Over the next few months we developed a relationship that was definitely not employee/employer. I spent more time in his room than I did in mine. He was extremely virile. As a result of our relationship I was named his sole heir provided that I always remain Francine. That clinched it in my mind. My parents would have to accept me as their daughter and they finally did. They never did know why I refused to revert to being Frank. My family finally met Mrs. Hamilton, my employer and visited frequently, never dreaming that she was a he. As his lover, I enjoy the finest clothes. My corsets are custom made. I am a guest at all of the social events she/he sponsored or attended. I accompany Joyce on her business and vacation trips. Some people might have wondered about the two ladies, one older, that were constant companions but most thought that we are just a well to do lady and her secretary/social companion, a not too uncommon scenario. I have the better of two worlds. In spite of my new position I do respond when I occasionally hear him say, “Take a letter (dear).”

Incidentally, my family eventually accepted Francine. Dad to this day still doesn’t understand why I wear tight corsets. However he strangely finds them fascinating. Whenever I have free time I love spending it with mom and sis. We of course go out as three ‘girls’. On occasion Joyce will accompany us for luncheon or a show. Once in a while dad and I will go out together. Am I guessing or have I noticed a look of pride on his face when a passing young man smiles at the pretty girl on his arm?

The End (?)


Sissy Girl Stories