The ad said: child care person wanted, full-time, live-in position, private quarters, use of car, light housekeeping, salary commensurate with experience. This sounded like an ideal position. I would have a place to live, a place to work on my book, and the relatively easy duty of taking care of a small child. The benefits sounded good...this is worth investigating.
The phone rang several times before being answered by a young sounding female. My mind was racing, rehearsing what I’d say.
"Hello Mrs. Duncan?"
"Yes."
"My name is Terry Parson. I’m calling in response to your newspaper ad for a child care person," I said, trying to sound interested though apprehensive about applying for a traditionally female position. I wondered what her reaction would be.
"Hello uh Terry...yes, well...the position is open if you’d like to come and interview," she responded with trepidation.
" I’m available this afternoon at 2PM," she added.
She hadn’t expected a male to call but she was legally obligated to consider me. I confirmed the time, got her address and made the appointment.
I found her house with no difficulty. It was in an upper class neighborhood, with well groomed yards, professionally landscaped, and very quiet.
I pushed the illuminated button in the center of the ornate brass plate. I heard the sound of a Westminster chime. Soon, the beautifully carved oak door opened revealing whom I assumed to be the woman of the house.
"Mrs. Duncan? Hi, I’m Terry Parson. I’m here about your ad for the child care position."
"Oh yes...come in please," she offered, "and my name is Pam. We want to keep this very informal."
Stepping aside, she welcomed me into her home.
She is an attractive woman, tall and slender, near my age, very well dressed for a housewife, I notice…casual but expensive casual. Her hair is well coifed, her makeup, perfect. I feel an immediate attraction to her. I am escorted into the family room of this beautiful home. It is well furnished, comfortable, a fireplace in the corner, and a wall of windows overlooking a wonderful view of the tree-filled backyard. We sit down and begin our discussion of the child care position as Pam pours me a cup of coffee from a carafe which had been prepared and placed on the appropriate coffee table. It was difficult to concentrate on the purpose of this visit, but I am to learn that she wasn’t a typical housewife.
"I have to admit, Terry, that I was surprised to hear a man inquiring about this position. I expected only women would apply. Have you had much experience caring for children?"
"Ah...Well not exactly, Pam...but I come from a large family where I was the middle child and had to share in the care my siblings while my mother worked to support us. But I’m confident I can care for your child as well as a woman and perform other duties equal to, or maybe even better than most women, especially when it comes to housekeeping. I’ve done my share of that too."
"Hmm, interesting point. But that remains to be seen. Really, why do you want this job? Forgive me, but it’s so, uh…domestic."
"To be perfectly candid, Pam, I’m a writer, and I’m working on a book. I figure I can write in my spare time, while this job would give me a place to live and especially a quiet place to write, and a little income to top it off. I think this would be an excellent opportunity for me in a domestic environment, and I know I would be a capable and responsible person to care for your child."
"An interesting point of view...I thank you for your candor, Terry. There is several points of view here. On the plus side, my child is a boy, and it wouldn’t hurt to have a child care provider who is male since he doesn’t have a father...I’m divorced and a single parent. So you would be a good influence on him. But, on the other hand, you don’t have any idea what age my son is so you don’t know how much time you’d need to devote to him. I don’t want to mislead you on your expectations of time to work on your book.
You have no experience as a Nanny, therefore you wouldn’t have any credentials or references for me to check. Also, it is a live-in position and I think it may be a little awkward to have a man living here. So you see, there are pro’s and con’s. However, let me consider the situation and get back to you. Please fill out this information form and let me review it. Thank you for stopping by."
When I completed the form, Pam escorted me to the door, we shook hands, and I departed. It was a short interview so I get no feelings one way or the other about whether I’d be hired, so all I can do is wait, but I am anxious to move in with this beautiful lady.
Work has progressed slowly on my book, and I am running out of funds and will need to find some form of employment very soon.
After a week had passed, Pam called and invited me to come back for another meeting.
"Hi Terry....I called you to return here for another discussion about the child care position. I’ll be up front with you as you were with me. I haven’t had a great deal of success with applicants. The few that applied were not eligible for various reasons. And, I don’t have a lot of time to pursue this...I have a busy schedule and a career to manage. I’ve checked your past employers and other references you gave me. In spite of the lack of formal child care experience as a Nanny, you’re the best candidate so far. Let me lay it out for you in detail....the job involves taking care of my son full time, he’s a year and a half old, as well as managing the household...some cooking, and shopping as necessary. I have a housekeeper for cleaning. You can hire people to help with the outside services if you wish. In general, you’ll be expected to manage the house as well as provide child care. You get your room and board, of course, free use of my cars, re-reimbursement for any household or child care expenses...just about complete autonomy since my business requires a lot of travel and long hours away from the house, so I have to trust you. You’ll also get a salary of $250 per week. Oh, and we will take occasional vacation trips at my expense with you in charge of Jerry, my son. Does that sound OK so far?"
"Yes it does, Pam...it’s a very generous offer." Too good, I thought...too good to be true, which meant there had to be a hitch. But she is still attractive to me. I listen to more.
"Now as I told you, I’m a single parent so it will be just the three of us here, and there-in lies a problem. I had expected to hire a female Nanny. I run my business out of my home office and frequently have clients visiting. I obviously cant afford to tarnish my reputation by having an unmarried man living here with me, so for the sake of appearances, if you accept the position, you will be required to wear a Nanny’s uniform and pass as a woman at all times. No one must know you’re not an actual woman. Looking at you, I think that wouldn’t be too much of a problem...you have very fine features, almost effeminate.... another reason I even considered you. If it’s ever discovered that you’re a male, it would mean a lot of embarrassment for me and instant termination for you. I realize this gender bending is a strange requirement, but it’s the best I have to offer. What do you think...are you interested?"
Everything was sounding great until she laid that last part on me. That was the hitch, but it wasn’t too awful. Dress and pass as a woman in a full time position? First the job sounded too good to be true, then comes another side I hadn’t exactly planned on. This is not a game...she is serious. But it is an ideal job offer otherwise. So what do I have to lose besides my identity, my gender, my.....?
"I don’t know about passing as a woman, Pam...I...I’ve never dressed as a woman."
Well, almost never, I thought...a half truth, but it was along time ago.
"I expected that...I’ll help you with the transformation if you’re willing. I’m pretty sure we can do it with your full cooperation. It’s important to me that you pass because you’ll be in contact with other Nannies in the neighborhood as well as my clients, service people and merchants, so you’ll have to convince everybody that you are a lady. On the other hand, you will have time to work on your writing as well as enjoy the benefits," she offered as an attempt to sell me on the idea. "You might even enjoy living as a woman," she added, smiling.
"Well, Okay, I guess...I’ll give it a try," I responded. "The position sounds wonderful, but I don’t know about this female impersonation thing."
I had to keep from biting my tongue as I had a memory flashback. I hoped my nose wasn’t growing longer.
"Oh, it wont be so bad... I’m confident we can pull it off," she repeated. "I’ll advance you your first month’s pay to buy you a woman’s basic wardrobe, and I’ll provide the uniforms I want you to wear. In this neighbor, the Nannies wear uniforms. Yours will be a black polyester dress with a white collar, black hose, and black flat heeled shoes. Oh…one other thing, Terry. You must sign an employment contract with me as protection for both of us. I had one drawn up in the event you accepted. It states that you will be employed only as long as your identity as a woman is maintained and kept secret to only you and I, as I mentioned. Also, you must remain in my employ until my son reaches the age of six and can start school full time. Any violation of those conditions means your employment will be immediately terminated and, as a penalty, you agree to pay the balance of any salary you will have earned up to the end of the contract. On the other hand, you are guaranteed a job for the next four and a half years."
Now I was to be indentured to live as a woman for the next four and a half years! Again, it was good job security for what I considered to be ideal conditions for a writer, but under unusual terms. My manhood for job security. With mixed emotions, I signed the contract.
With my only possessions packed into two suitcases, I moved in the next day and the transformation began immediately. After taking measurements of my body as a dressmaker would, Pam, little Jerry, and I went shopping for my new wardrobe. Pam selected some basic items of assorted underclothing, narrating as we went along although I was too busy with Jerry to pay her much attention. Underpants in both cotton and nylon so I could decide which I prefer, bras with padded cups and additional enhancement pads, slips, both half and full, hosiery in different colors especially black, both pantyhose and thigh-highs. It seemed as though she was buying these things for someone else so I went along with her selections rather disinterested. We went into the ladies dress area and she picked out several dresses, skirts and tops, slacks, and shorts, occasionally asking my opinion of things. I just agreed with everything she said. I had no idea what she was muttering about. I was carrying Jerry and keeping him content. He required all my attention since he was soon bored. Our next stop was in the shoe department where she purchased some women’s casual shoes for me as well as some medium heeled leather pumps and my uniform shoes. She commented that we both wore the same size in many items...that might prove convenient. We finally ended up at the cosmetic counter. Pam picked an assortment of cosmetics and makeup items for me. I had no idea what she bought, but she knew and that was all that mattered. Departing the mall, we made one more stop at a wig salon. Pam told the sales associate that I needed a wig for a woman’s part in a play I was to be in so I was fitted for a suitable wig in my own hair color. She chose a style that would be easy to maintain, namely a page-boy cut, short, with bangs. The wig enhanced the feminine features in my face....Pam was right.
Back at the house, we unpacked our purchases, removed price tags, and found places for everything in the closets and drawers in my room, a spare bedroom Pam had furnished as a Nanny’s quarters. Expecting a female Nanny, the room was decorated for a woman. All in pink and white colors, lots of lace and chiffon...lace trimmed bedcovers and skirts on the bed and furniture, chiffon curtains and lampshades. Pink flowered wallpaper with little red roses...I thought, ‘how appropriate for my new lifestyle’. Even my bathroom had pink fixtures and gold trim. All very nice. It gave me a sense of deja vu.
Pam instructed me to take a hot, soaking bath, shave any body hair and change into my new clothes. I was to call her if I needed help with dressing but I said I didn’t think that would be necessary since I had been raised with sisters. I took a long hot bath, during which time I shaved my legs, arms, underarms, and chest clear of what little hair I had. I also shaved my face taking pains to get a very close shave. I knew she’d want me to do that in preparation for some makeup. When I was finished, I gently dried myself off and applied fragrant body powder she had bought to my baby smooth skin. It felt strange being so hairless again, but that was only the beginning. I stepped into a pair of nylon panties and pulled them up. The cool, soft fabric felt wonderful against my skin. I next selected a pair of nude colored pantyhose and, while sitting, placed a foot into one leg, gathered up the material and rolled it up my leg half way. Then, I repeated the same maneuver for the other leg, at which point I wiggled the remaining part of the hose up to my waist. I didn’t recall that pantyhose felt so good, and they made my legs so shapely. I took a bra from the drawer and, placing my arms into the straps, gathered it around me and hooked the closure. Pam had the foresight to buy me front closure bras. Even though the cups were padded, there was still a need for more so I filled them with the extra forms. Now I had a female figure and I cant say I didn’t like it. I stepped into a half slip and pulled it up to my waist, followed by a skirt and a rayon blouse. The uniform dress would come later. I had a little trouble with the buttons on the blouse because they were backwards for me, but I knew I’d get accustomed to that in time, again. The way the blouse conformed to my breasts caused me to bulge under my skirt urging me to rub my manhood but I didn’t want to start something I couldn’t finish. Fortunately the skirt was full enough to conceal it. I next stepped into a pair of pumps with 3"heels, and placing the wig on my head, I checked myself in the mirror before presenting myself to Pam. I was satisfied with my appearance...at least I was presentable. I not only looked good, but I felt good. I liked the feeling of these garments. I thought I’d be embarrassed dressed this way in front of Pam...but I wasn’t. Having to wear these things all the time isn’t going to be bad, I thought. With a few practice steps around my room, I walked out to show Pam.
"Wow Terry...you do make an attractive woman. I knew you could do it. How does it feel to be wearing a skirt?"
"Surprisingly comfortable, Pam. I think I could learn to enjoy this," I replied convincingly.
"Well, I’m glad you feel that way...you’re going to be wearing those things for a long time," she said, smiling. "Let’s get some makeup on you to finish the look."
We went into the master bathroom which was a large room with a large Jacuzzi equipped tub and a separate shower stall, and a large vanity with lights surrounding a mirrored wall.. Pam sat me down in front of the mirror where she had an assortment of cosmetics arranged. She complimented me on my fresh shave as she began to apply a foundation creme with a small sponge, working it into all the details of my face and neck. As she applied each item, she described what she was doing and the purpose. She worked on one side of my face and let me do the same to the other side so I’d learn how. I tried to be amazed at the metamorphosis that was occurring as if it was the first time. When she had finished, I was looking at a beautiful woman! I did indeed feel delightfully feminine.
"You’re a natural, Terry. You’re very pretty as a woman! You’ll have no problem passing and I think you’ll enjoy it. We don’t even have to change your name. So, how do you like your new look?"
"What can I say, Pam, it’s not bad...not bad at all," I understated, as I viewed myself from all angles. I found myself speaking very softly. Pam sensed the change in my tone of voice.
"Let’s begin work on teaching you the basics," Pam said as we went into the family room.
She proceeded to instruct me in how to sit properly, walk graciously, how to gesture like a lady, how a lady speaks...voice control, eye movements, facial expressions, and feminine vocabulary. I didn’t recall there being so much difference between genders. Like all men, over time, I had taken women’s actions for granted. But now I had a vested interest to learn. I made a conscious effort to practice everything Pam taught me since I looked and felt the role. Wearing a skirt was very different than pants. It patterned my behavior and movement. I had to keep my legs together while sitting out of sheer modesty, and it governed the way I walked...the way it swirled around my legs limiting my stride. I enjoyed it. We practiced until late that first evening. At bedtime, Pam reminded herself that she had forgotten to buy me nightclothes so she gave me one of her nightgowns to sleep in. It was a pink nylon, full length gown with modest lace trim and a perfect fit as she knew it would be. I removed my makeup with cold creme and hit the pillow. That night, I slept like a baby in this free-flowing and comfortable garment. This new lifestyle was going to be all right, I thought. I just had to revamp my thought processes. I still found her to be a very sexy woman, but now, with me as a woman, how could I attract her to me? Would she see me as a male? And what kind of a man dresses as a woman? So confusing….sleep came.
For the next two weeks, each morning, I eagerly got dressed, applied my own makeup, and, after taking care of Jerry, practiced Pam’s instructions of how to properly walk, sit, and gesture in a ladylike manner. She constantly reminded me if I slipped up on anything until it became instinctive. When my uniforms arrived, I changed to the new dresses. By that time I was adjusted to wearing a skirt and the modesty required with it and I found them to be quite comfortable and a minor encumbrance. Worn with a padded bra and black pantyhose, they were very stylish and feminine. Pam had good taste.
Pam stayed with me during that period so we got better acquainted with each other and she established a level of confidence with me. We related to each other as two women as I worked to forget my recent past and concentrate on the present. Very little progress was made on my book while I focused on my transformation. I found myself really getting into learning to be a woman...almost wanting to be a woman. Pam had become very persuasive about my transition. She was a good salesperson.
Finally, Pam had to go to visit a client for a meeting and I was to be alone with Jerry for the first time. That didn’t bother me, but what if someone came to the door. That concerned me because I didn’t want to jeopardize my position by not being a convincing woman. Pam reassured me that there would be no problem. She felt I was completely passable as a woman. As it turned out, there were no visitors that day, but all afternoon, while Jerry napped, I continued to practice my acting as a woman, while pretending I had guests. I knew I should have used the time for writing but I was too concerned with my appearance to concentrate on anything else. But it was paying off...my confidence level of being a lady was rising.
One afternoon, I was preparing lunch when the doorbell rang. It was a salesman for a lawn service. He accepted me as the Nanny of the house immediately. He was very courteous and not the least bit suspicious, but then why should he have been? My first contact with another person as a woman and I passed. I was pleased and relieved. I told Pam what happened and she suggested we go out in public, perhaps to dinner to bolster my confidence. I changed into something appropriate, freshened my makeup, prepared Jerry for the excursion, and we went to a restaurant. Things went very well, I tried hard to act like a lady, which was now fairly easy, and didn’t get a second glance from anybody, including the waitress. Pam was very pleased with me. I knew it was important for me to pass...the contract was hanging over my head. As luck would have it, Sarah, the Nanny of Pam’s neighbor spotted us and came over to say hello. Pam introduced us and invited her to visit us at the house. Sarah was pleased to meet me and promised to do so. This was to be my real test...to be accepted by a real unsuspecting woman. After dinner, we returned home to put Jerry to bed and review my evening. I got a glowing report from Pam. She said I was doing a great job with my transformation, better than she had expected, and she was pleased with my Nanny work. She had no remorse about hiring me for the job. We were becoming good friends, but it was a woman to woman friendship. She treated me as a sister as we discussed feminine things such as makeup, styles of clothing, children...girl-talk. I never talked to her about household things. I just took care of them on my own. My hope of a male to female relationship with this gorgeous woman was diminished.
Within a week, Sarah came to visit with Jamie, her charge. We spent the afternoon talking and getting acquainted while the children played. I was extremely careful how I acted and spoke in her presence. She gave no indication that I was anything but another female...it was all girl-talk with her also. At first, I was a little nervous, but I soon relaxed and enjoyed her company. For someone who had not worn women’s clothes for a long time, I was now able to be in the company of another woman as a woman and feel like a woman. It became so natural. For a few fleeting moments, my male thoughts turned to wondering what she’d do if she knew what was really under my dress, but those thoughts quickly disappeared as I mentally accepted that I was a lady. We became good friends, and through her, I met the other Nannies in the neighborhood. I was accepted as a woman by all of them, and in their company I further honed my skills of presenting myself as a genetic woman. We met frequently for coffee and gossip which provide me with the opportunity to learn the methods of socializing as a woman. I made a conscious effort to learn. Sarah accompanied me to get my new driver’s license as a female. I told her I was new to the state and needed it. She never doubted otherwise....nor did the officials at the license bureau.
Within a few months, my hair was long enough to rid myself of the wig and maintain the same pageboy style. With Pam’s assistance, I had groomed my eyebrows to a feminine shape. Pam asked me if I’d consider permanent removal of my beard and other masculine body hair. I readily agreed to it so she arranged laser treatments for me at her expense. In less than three months, my beard was completely gone, my eyebrows were permanently arched, and they were almost completed with my chest and legs. In time for a summer vacation.
I was completely acclimated to the job of managing the household and caring for Jerry as well as to my new identity as a woman. My effeminate actions were instinctive now...I think I had completely forgotten how to be a man anymore and I didn’t care. Pam was right...I was quite comfortable living as a woman. So when Pam invited me to accompany her and Jerry on a trip to Cape Cod for two weeks, I eagerly accepted. Of course my Nanny duties continued, but it was still a vacation since Jerry was so little trouble. He was like my own son and I was like his mother. And I was to travel in regular street attire.
We stayed in a hotel in Provincetown, spending time shopping, browsing the antique stores and walking on the beaches. During Jerry’s nap time, I continued work on my book. Pam cared for Jerry for a few nights while she let me attend some female impersonator shows of which there were plenty. The boys were lovely in their presentations as women, singing, dancing, and generally enjoying themselves in their pseudo gender.. I could appreciate what they had to do to look like that, but I had no regrets about the effort I had to go through. I had the advantage of not having to switch genders every day. Even the transvestites accepted me as a genetic woman...I had fooled everyone. When I told Pam, she was delighted...and so was I. She said I had passed a test by masters of the craft of gender switching.
I mustered enough confidence to purchase a swimsuit and wear it while walking on the beach. It was a rather conservative design but still somewhat revealing...a big step for me. I had to fill the bust cups with foam forms but it looked very authentic. Pam said I looked perfectly lovely and I had to believe her. I did get a few admiring looks from men along the way, and that pleased me. I would have been disappointed if they hadn’t looked.
During this trip, Pam and I had a chance to talk about our pasts. I learned that she had been the victim of a bad marriage and a bitter divorce. She was really down on men now. She vowed never to have anything to do with them again. She had been burned once and that was enough. I had to ask how she felt about me. I was still a biological male, and I still had male feelings towards her. She replied that she didn’t consider me a man anymore and felt very comfortable with me in my new persona. My transition was complete. She accepted me as a woman. She proved it by changing clothes in front of me in the hotel without any display of modesty. My femininity came forth when I could view this beautiful lady in her undies and not get aroused...after all, I was wearing the exact same clothing as she was. I now lusted for her, but not as a man for a woman but as a lesbian.
I finally admitted to Pam about my past. I was the only boy in a family of eight kids. Being a middle child and my mother being the sole support as a widow, we had limited income so I was forced to share my sister’s clothes as much as possible. For the most part, I was raised as a girl since I spent most of my childhood in girl’s clothing, going to parties, church, social events in pretty dresses and to school in mostly androgynous attire...boy’s things on the outside, girl’s underneath since my boy clothes was so limited.. I grew to enjoy being a girl since I hardly knew any other way of life and had only female playmates until I was too old to conceal my masculinity. In my early teens, I even dated a few boys with my older sister’s help. They made me very feminine. My transition to manhood was difficult. I took to writing because I had limited skills in other areas while writing came easy for me.. This domestic position was a natural for me so I applied and fortunately got the job. The requirement to live as a woman was a bonus I hadn’t expected. I admit, I love living as a woman again.
"Ah...I noticed you took to the transformation easily and you were a very fast learner," Pam disclosed.
"I’m happy you’ve found yourself...I’ll do whatever I can to help you, Terry."
My admission drew our friendship even closer. The second week of our stay in P-town, Pam canceled my hotel room and had me share her room and her bed. It just seemed so right. We slept as sisters...no...lesbian lovers. We kissed, embraced, and made love in every position without penetration other than orally. It was fulfilling to both of us...it was beautiful. Our vacation ended too soon but our relationship didn’t.
Our bond became intense. At home, Pam was the "husband" and head of the household, while I assumed the role of the "wife", and of course Nanny to Jerry. I moved in with Pam, shared her bed, and satisfied her any way a lover should. It wasn’t a business relationship anymore...it was a marriage and I was the bride...I loved it...I loved Pam.
She shared her entire wardrobe with me, dressing me in many of her fancy dresses which I would wear to model for her. I was completely comfortable while attending her parties wearing a cocktail dress with high heels and dark hosiery as a maid to serve her guests. It was at one such party that a gentleman client approached me and asked me out for a date. Pam whispered to me that I should accept...it would be favorable for her business...so I did. I had been living as a woman long enough so I wasn’t worried about being discovered...in fact, I was very relaxed with the prospect of dating a mature man. He made me feel very feminine, extending all the courtesies a gentleman does for his lady. I loved the attention. The date ended with a warm kiss, my first kiss by an adult male, and I enjoyed it! That was the prelude to another date and more kisses and some petting. I enjoyed the sensation of being held and kissed by a man...but knowing it could go nowhere, I ended it before we got emotionally involved. But I did continue to casually date other men. I loved being the target of men’s affections, being pursued, romanced, seduced. It was wonderful. I learned to pleasure a man in a very ladylike fashion, after all, only a male knows what pleasures a man the most, and I got very good at it. And I could conceal my maleness well enough to give them some liberties. I was very careful about that.
After my first dating encounter, I asked Pam if there was anything I could do about enlarging my breasts. I was becoming self-conscious about wearing breast forms, especially when a man was holding me. Even the good silicone forms were not enough anymore…not very lifelike. She suggested breast implants. We talked to her doctor friend who agreed that was the best way. Hormones were too dangerous, too many unpredictable side effects. So the procedure was scheduled and I received a set of breast implants which allowed me to amply fill my bra’s C cup with my own flesh. They looked wonderful and I was so proud of my new figure. Especially since there was so little discomfort with the surgery. Now I had genuine cleavage...not just an illusion! And the tactile sensation was heavenly. Pam was as happy as I was and couldn’t leave her hands off of them as much as I loved her touch. I could now wear her dresses with the lowest necklines...a whole new part of her wardrobe. I loved my new body.
Jerry was getting big now, almost 4 years old. One day, I noticed him playing in our room. He was walking in my high heels, with a nylon stocking around his neck as a scarf, and had lipstick on his face. He said he was playing mommy. I asked him if he wanted to look like a little girl...like Nanny, to which he replied, yes. I cleaned his face of the smudged lipstick, removed his boy clothes, and put him into a pair of panties and stockings, pinning up the extra material for a fit. Then a slip, gathering up the surplus and tying it with a bow to look like a gown. I carefully applied fresh lipstick, blush, and eye shadow, making him into a darling little girl completed with a ribbon in his long curly hair. He happily stayed that way until Pam came home. When she saw him, she laughed and hugged him.
"I didn’t know I had a little girl. You’re beautiful, Jerry. Do you like those clothes?"
"Yes Mommy...this is fun. Nanny dressed me. Now I can be like you and Nanny."
I apologized to Pam for doing that but she smiled and said it was perfect. It made me happy wearing those clothes...maybe Jerry would be happy, too. She was in no hurry for Jerry to change. She let him play it out, but he stayed that way till bedtime. I told Pam it was Jerry’s own idea to cross-dress. He had played with my things before, but this time he dressed himself so I helped a little. We wondered if he wanted to do more of it. The next morning, he asked me if he could do it again, but I told him my clothes don’t really fit very well and that we’d buy him his own things. He accepted that. Later, I again found him wearing my lipstick and shoes. I called Pam to tell her what happened. When she came home that day, she had bought Jerry some new clothes. She figured he would just secretly wear our things anyway so let him get it out of his system now. She bought him little girl’s panties, petticoats, a dress, and shoes which he immediately put on and came out to proudly model for us. With his long curly hair, he did indeed look like a little girl. He continued to dress that way for the next few days until I was able to discourage him by making him do girl’s chores.
I talked with the other Nannies, during our routine coffee sessions, about Jerry’s behavior towards cross-dressing. Some of the others had heard of it, but none had first hand experience. They thought maybe because there were no male figures in the household. But then some had girls who never wore dresses and played with boy’s toys and games and never thought anything unusual of it. So why were we so disturbed about Jerry? He’ll likely outgrow it as the girls will. Somehow, I wasn’t so sure....I never outgrew the proclivity.
Pam wasn’t helping...she continued to buy Jerry girl’s things. She thought it was fun, the stuff being so cute. Jerry loved them...I’m not sure whether because they were just new items or because they were girl’s things, and he continued to wear them and slowly began to act very effeminate while Pam encouraged it.. My threats of doing girl’s chores no longer worked...he jumped right into the tasks at the mention of it. I think Pam was allowing this to happen as her way of getting back at men. She had made me into a woman, now she was doing the same to her son, and I was helping her.
For Jerry’s fifth birthday party, we invited the neighbor’s children and their Nannies, of course. Jerry was now wearing girl’s things frequently and behaving accordingly. Since all of the other children were girls, he fit right in with them and they played together so well. He was receiving no male role model support...certainly not from me. Trying as hard as I could, well, not too hard, I couldn’t prevent Jerry from wanting to be a girl so I gave up completely. Pam and I discussed taking him for counseling as a last resort to ease my conscience, but she wanted to wait until it was closer to him starting school....another year. At that time, my contract would be up and I could leave, although I don’t know where I’d go. I was happy here, I loved Pam, and I loved being a woman...I knew I could no longer live as a man anymore nor did I want to be one.
We continued to let Jerry behave as a girl or a boy, whichever he chose, not unlike the genetic girls. He chose to play only with the other girls and they accepted him as one especially when he dressed the part. Pam let him...encouraged him to wear makeup and play dressup, complete with jewelry, nylons, pretty dresses. she bought him everything including feminine toys and games. She was completely feminizing her little boy, I think to get back at Jerry’s father. Whenever I’d remind Jerry that he was a little boy, he’d cry, deny it, and if I pushed it, he’d say he wished he was a girl...he didn’t want to be a boy. I knew we were in trouble.
I finally convinced Pam to take Jerry to a counselor who decided, after extensive testing, that Jerry was indeed confused about his gender. Of course I didn’t mention about Pam’s encouragement for the child to be a girl. He had developed all the characteristics and attitudes of a female, and to regress back would be very difficult and harmful to his interpersonal relations with other children of both genders. Pam talked to her doctor friend about Jerry, seeking medical advice...perhaps a sex reassignment to make the body fit the mind. The doctor said that because Jerry was so young, nothing radical should be done now except to continue raising him in the gender of his choice…as a girl. When he approaches puberty, they could block his male physical development and cause him to develop as a female. Later, surgery would finish the re-assignment. So, Pam agreed to that and made plans for Jerry to attend private school as a girl.
In the Fall of Jerry’s 5th year, Jerry was enrolled and started a private school as a little girl. His name was legally changed to Jeri. My contract with Pam as Jeri’s Nanny was completed and I was free to leave. Pam extended the offer for me to stay with her as her assistant in her business with the same terms as before, which I readily accepted. I would have married her but she would have no part of that so we remained together as lovers. In my mind, I was a total woman and would never change back to being a drab man.
Jeri socialized as a girl, and, upon reaching puberty, began a hormone schedule to allow her body to become that of a woman. She evolved into a beautiful teenage young woman. After high school, she had sex reassignment surgery to become a legal female. She never learned my true gender, but always considered me a woman....her Nanny.
I never did complete work on my book.
© 2000
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