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The Awakening of Evelyn

Author: 

  • Evelyn D. Fairechild

Organizational: 

  • Title Page

Audience Rating: 

  • Adult Oriented (r21/a)

Taxonomy upgrade extras: 

  • crossdressing
  • Posted by author(s)
  • Novel > 40,000 words

The Awakening of Evelyn

by Evelyn Fairechild

The Awakening of Evelyn - Book 1

Author: 

  • Evelyn D. Fairechild

Audience Rating: 

  • Adult Oriented (r21/a)

Publication: 

  • Novel Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

TG Themes: 

  • Voluntary

TG Elements: 

  • Chastity Belts
  • Dominance & Submission / Bondage
  • Fancy Dress / Prom / Evening Gown
  • Hair Salon / Long Hair / Wigs / Rollers
  • Jewelry / Earrings
  • Panties / Girdles
  • Retro-clothing / Petticoats / Crinolines
  • Sissies
  • Turned into an Object
  • High heels / Shoes / Boots / Feet

Other Keywords: 

  • lingerie
  • Petticoats
  • Soft Sweaters
  • Boudoir
  • Kept
  • Silk Stockings
  • Cosseted

Permission: 

  • Posted by author(s)

The Awakening of Evelyn

Book 1

Evelyn D. Fairechild


A delicate teenage boy discovers his love of crossdressing and is encouraged by his aunt, mother, and his mother's best friend.


Chapter One — My Secret

I had a happy childhood, or at least I wasn‘t unhappy, in spite of my gender issues.


My father was an aristocratic Englishman, and passed away when I was young. My mother, from the San Francisco Bay area, was loving and kind and raised me well. She was half Vietnamese and half Norwegian, and very beautiful — she had worked as a model, and probably could have obtained ’super-model‘ status if she cared enough to try. My friends would tell me how ’hot‘ she was, much to my chagrin. She had a fragile and somewhat passive personality and abhorred confrontation — she would leave things unsaid rather than deal with issues.

A couple of years after my father died, my mother became a trophy wife to a successful investment banker. My relationship with my stepfather could best be described as cordial. He did not have any children of his own, and was not the least bit interested in having any. He was never mean to me — mostly disinterested, but he did teach me a lot about investing and money management. He was often absent, spending part of the week in New York and the other at an office in Philadelphia, near our home.

Both my natural father and mother were wealthy as well. When my father died, he left me a trust fund, administered by my mother and her half-sister, my Aunt Beverley, which was worth many millions.

My mixture of English, Norwegian, and Vietnamese heritage resulted in me having slightly almond-shaped eyes, delicate features, brunette hair, blue eyes, and a very pale and fair complexion. I was frail and slight as a youth, with childhood asthma, and, much to my embarrassment, prone to bedwetting. My heritage and physical stature gave me a very girlish appearance and my voice was high pitched and soft — puberty didn‘t seem to change it. I had a full head of luxurious brunette hair, with a natural wave and curl that not a few ladies told me they‘d ’die for‘. In certain situations, such as accompanying my mother to the mall, or wandering through the ladies clothing section of a department store (which I loved to do, but made me so very nervous), I would be mistaken for a girl.

I was christened Evelyn Dale Fairechild. In today‘s world, Evelyn is a girl‘s name, but it wasn‘t long ago that it was a fairly common boy‘s name (witness Evelyn Waugh, the writer), and Evelyn had been my fraternal grandfather‘s name. I went by my middle name, and if anyone asked me what the "E" stood for, I‘d say Evan.

I attended a private school near our home in southeast Pennsylvania. Being shy and not at all masculine, I never had a girlfriend, and remained a virgin throughout high school. I loved music - piano and guitar — and was quite talented. My few friends were fellow musicians, and played in a couple of really good high-school bands. Some of my friends were the wrong crowd by mother‘s standards, and I guess she was right because we did experiment with drugs — mostly cannabis. I developed a taste for hashish, but eventually, I mostly gave it up — it gave me long and unwelcome bouts of paranoiac self-examination — anxiety attacks. At the beginning of my junior year I contracted hepatitis and then pneumonia. Partly because of my illness and partly because of my genes, I had stopped growing at five feet six inches, and a hundred and fifteen pounds, the same height as my mother. I had to repeat most of my junior year, which meant that I would graduate a half-year after the rest of my class. My illness may have had something to do with the fact that I was a ’late bloomer‘, not reaching puberty until I was almost eighteen.


I can‘t remember when I first started crossdressing. All I know is that I started sneaking into my mother‘s room whenever the opportunity allowed and dressing in her things. She had a separate bedroom from my stepfather, which she kept most femininely decorated. She called it her ’boudoir‘. She had lovely things — fine lingerie from Europe, designer couture fashions, many of which she was given as part of her modeling, and a small ransom in jewelry; pearls, emeralds, lapis, diamonds, sapphires, and artisan jewelry. When I dressed in her things, the feeling of silk, lace, and fine fabrics next to my skin sent exquisite chills through my entire being. The utter femininity of her things gave me such pleasure. The fact that they were my mother‘s clothes never played into my fantasies, just the exquisite pleasure I felt being dressed as a lady. I loved wearing foundation garments - brassieres, garter belts, stockings, and, above all, delicate panties. I would almost swoon while wearing these things. I heard my mother say on more than one occasion that she hated pantyhose, saying that she disliked the way they felt and that they gave her a rash. She much preferred stockings, preferably silk, and she would order them through the mail. But for all those dainties, dressing up just wasn‘t complete until I was wearing one of her fancy dresses and all made up, in high heels and jewelry — all the accessories that made a lady a lady. I felt so wonderful, so content, so alive and erotically charged (even as a prepubescent), so very naughty. I knew that something was terribly wrong with me and that I could never, ever divulge my secret. My crossdressing always brought about feeling of shame.


My mother received all sorts of ladies clothing catalogs and fashion magazines, and I would sneak off and study them in my room. I would also browse the websites that my mother visited, but because she had installed a very secure search filter on our computer, I was never able to discover any crossdressing communities or websites. Nonetheless, I became literate in fashion terms, and found that some terms had conflicting definitions, so I refined my own vocabulary. For example, the definition of a petticoat, to me, meant a long half-slip, intermission length (to the mid or low calf), tea-length (the low calf to just above the ankle), and floor length (to the ankle). To others, a petticoat meant any half-slip made of crinoline. A crinoline, in my world, meant a half-slip of any length, made of that wonderful rustling fabric, meant to pouf out a skirt, with flounces of lace at the hem. A petticoat, on the other hand, would be made of a fluid material, such as silk, and should be prettily decorated with lace and embroidery — a true underskirt. A pettislip was a petticoat that was just below the knee or above — ’street length‘ in some vernaculars. A peignoir was a full-length (to the ankle) garment meant for sleeping, and was a dramatic gown meant to wear in bed, made of sheer fabrics, such as silk chiffon. A nightgown differed from a peignoir in that it could be made of non-sheer fabrics, such as silk charmeuse, with a wide range of styles — essentially an evening gown made of lingerie fabrics. A negligee was anything longer than a chemise and had a fitted bodice and straps. Negligees were just fancy slips, meant to be alluring, and could be for bedtime or under dresses. All of them, of course, were to show a lady at her most feminine and to arouse passions.

The underthings that ladies wore were so fascinating, and I thought that they were at least as important as a lady‘s outwear and accessories. Dressing properly had to begin with the underdressing, which started with foundation garments; brassiere, garter belt, and immodest panties, all perfectly matched. And to me, foundations should include fanciful garters that matched the other foundation items, one on each thigh to cover the top of the stockings so to hide the clasps of the garter belt suspenders, rather than just for support the stockings. The garter belt itself should be wide, as traditional garter belts, sometimes called waspies. Over the foundations, a real lady should wear another pantie — or more — to cover the immodest bikini, such as a French cut brief or a tulip pantie. Topping it all off was a set of what some used to call daywear: camisole, pantie, and pettislip or petticoat (depending on the length of the skirt). Like foundations, these articles were a matched set, and should be fancifully decorated with lace, embroidery, or other feminine embellishments. A daywear set could be worn as outwear, except for the fact that they were far too feminine for a modest lady to be seen in. The outermost pantie should be a tap or dance pantie, a dance pantie being cut fuller and longer than a tap pantie. Perfection would be that the foundations and daywear should all match. During my furtive crossdressing‘s, I found myself wearing more and more panties. I would try to find panties that were of similar color that would overlay each other, the one on top completely covering the one beneath. Donning panties and drawing them off was so thrilling to me, watching myself in the mirror, fixating on the delicate lace. The more panties I wore, the more thrilling and naughty it was for me. I rationalized the wearing of so many panties as a way of adding fullness to my hips and derriá¨re, and the psychologist in me told me that the layers of panties would hide my maleness.


Mother‘s best friend was a French woman named Mimi, a handsome lady with a calm inner strength and air of authority. Mimi and mother had been friends when I was in elementary school, but she moved back to France for a number of years, and then moved back during my junior year when I was ill.

Mimi often babysat me when I was young. She was a few years older than my mother. I used to call her ’nanny‘. We had a warm relationship, and she would address me as "dear" or "sweetheart" and, sometimes "mon chéri", using her French. She could never seem to pronounce my name correctly and called me ’Dahl‘, which sounded almost like ’doll‘. She was taller than mother or me, and dyed her bobbed hair jet black with a broad streak of white. She was often impeccably dressed and groomed and dressed conservatively in nice clothes. When she returned from France, mother, through her modeling contacts, got Mimi a couple of jobs as a model for mother-of—the-bride gowns featured in a bridal magazine. When mother showed me the magazine with Mimi‘s photographs, I was amazed — Mimi looked fabulous and I was jealous that she got to wear such beautiful gowns. I always wondered why she never married — she was certainly good-looking enough to attract a man‘s attention. Like my mother, Mimi attracted the attentions of my friends.

When I was sick, Mimi would do laundry, a little vacuuming, make the beds, and generally tidy up, but mostly just hang out with my mother, allowing her to care for me. For heavier housework and cleaning, we employed some ladies who came by every couple of weeks.

Mimi had an apartment not far from ours. When my stepfather was gone for the night, which was fairly often, she‘d quite often stay overnight in our downstairs bedroom, originally the servant‘s quarters that had its own bathroom, closet, and a fireplace, which Mimi loved, especially on winter evenings. Mimi was "well enough off" as mother put it. Nonetheless, she worked at an art gallery and dabbled in real-estate.

I never thought that the relationship between mother and Mimi was anything but platonic, but, on occasion, I would find them in more intimate positions when they thought I wasn‘t around, such as Mimi sitting on the couch with mother‘s head in her lap, gently stroking my mother‘s hair, or embracing each other in a quiet corner. I guess I was just naíve — in retrospect, it was evident that they were lovers; they just did a very good job of hiding it from me and my stepfather.


There were a few occasions when I was crossdressed by mother and Mimi, although it was moderate and, by all outward appearances, innocent. Mimi said she had a niece my age in France who was, according to Mimi, about my height and build — which meant skinny. When I was still in elementary school, I came home one day to find a girl‘s skirt and sweater set laid out on our living room couch. I was told that they were gifts for Mimi‘s niece that mother and Mimi had purchased that afternoon (which explained why the price tags were still attached). The set was a peach and gray pleated tartan skirt, peach cashmere twin-set, and a pair of woolen peach pantyhose. Mimi expressed concern that she didn‘t know if the things would fit her niece and she asked that I try them on for size. It seemed like an odd but innocent request, but I (of course) objected. Mother admonished me and told me to help Mimi and do as she asked. "Besides" she said "I bet you‘ll be cute". So I went upstairs with the skirt and twinset and dressed. There was nothing but my boring boy underwear beneath and I didn‘t even get to wear the pantyhose. Although I was in principle crossdressed, there was no thrill. I came downstairs and goofed around a bit. Both mother and Mimi said I looked cute and mother even said, to my chagrin, "we should dress you all the way with makeup and heels and some padding — you‘d easily pass as a girl." After a minute or two, Mimi was satisfied with the fitting and I went upstairs and undressed. The entire incident (except for mother‘s comment) seemed innocuous and harmless and I didn‘t give it much thought after that. A few weeks later, Mimi mentioned that her niece really liked the set and it fit her perfectly. Once or twice after that, Mimi (with mother‘s assistance) would buy her niece an outfit and have me try it on for size. Each occurrence was basically the same — I‘d try on the outfit in my room, pause to admire myself, and then go downstairs to have mother and Mimi evaluate it. They would tease and joke with me a bit and, although they would suggest ’going further‘ with the dressing, never did carry through with it, mostly because I vigorously protested (I would have loved to have ’gone further‘ with it all, but the puritan in me shut down those desires).


Chapter Two — My First Sojourn

I‘ll never forget the first time I had an orgasm (which I called a "creaming" — a more delicate term, I thought) while crossdressed. The few creamings I had to that point would start by browsing through a fashion catalog or two, dreaming of wearing the beautiful dresses shown inside. At first, I would lie in bed, stomach down, on a pillow covered with a soft towel to prevent staining the pillowcase, slowly churning, dreaming about being dressed. Later, I discovered the pleasure of lotions and strokes of my hand. I had to be careful with this method because my cream could expel rather far, as I discovered one night when I had to wipe a puddle or two from my face. I found out later in life that I was unusual in this regard, which may have explained the intense and deep satisfying pleasure I experienced with creaming.

My first experience of creaming while dressed was spring of my senior year, not long after I reached puberty. My parents were gone for a long four-day weekend. Mimi was to check up on me and make sure I had ready-made meals, but, much to my relief, she wasn‘t spending the night — something about ’previous commitments‘.

My parents left on a Friday afternoon. Mimi was there to see them off, and then fixed me dinner. After assuring her that I would be perfectly fine by myself she left me for the evening. I scampered upstairs, showered, and then snuck into my mother‘s room. There on the bed, carefully laid out, was a tea-length gown with a matching bolero jacket and a petticoat. The gown had a black velvet bodice and an empire waist tied with a midnight blue satin ribbon that matched the midnight blue silk faille of the skirt and jacket. The petticoat was white with a double layer of tulle lace netting at the hem. Why had my mother left it there? Was it something she meant to pack, but didn‘t? Did she know about my crossdressing, and left it for me? I didn‘t have an answer, but it was definitely on my mind as I found myself, a delicious couple of hours later, all dressed, accessorized with a fine pearl necklace and bracelet and black velvet pumps. I was made up in lipstick, mascara, and blush. Beneath it all I wore a matching antique white lace brassiere, garter belt and French pantie set, a soft bit of terry cloth protecting my ’daintie‘, black seamed stockings, an antique-white silk camisole and dance pantie, and the exquisite petticoat. The petticoat absolutely thrilled me, and I wore it so that the tulle lace hung an inch or two beyond the hem of the skirt. I was standing by the recamier, cheval mirror in front of me, primping and swishing, reveling in the rustle of the petticoat, and my hand wandered down. I was so stimulated by that point that it only took a few gentle strokes of my finger across the dress in front of my daintie to entice a withering creaming. I cried out as wave upon wave of exquisite pleasure swept over me. (It was pure luck that the terry cloth absorbed most of my cream. As it was, I had to wash the panties, but it could have been much worse, with cream on the dress.) I couldn‘t believe that anyone could possibly feel that much pleasure! From that moment on, I knew absolutely that there would be no denying the deep exquisite pleasure I had just felt.


On Saturday, I dressed in a recent purchase of my mother‘s — a beautiful pink chiffon robe and nightgown, a diaphanous lovely by Jonquil. Beneath I wore a pink brassiere, garter belt, stockings, bikini panties (again, with a small linen towel protecting my daintie), and silk tap panties, finishing off with ankle-strap high stiletto heels. Just before finishing my makeup, I smoked some hashish and got really high. Like the last couple of times I got high, paranoid thoughts bombarded me as I sat at the dressing table — an anxiety attack, I guess. I somehow finished making up, the lip-gloss the final touch. Feelings of utmost shame and humiliation swept over me as I sat there, dressed up in ladies things. Oh, what a sissy I was! What a rich, spoiled, crossdressing sissy, a ’Nancy‘, a pampered and prissy pantywaist! Oh, how would I ever amount to anything? While other boys were out chasing girls and playing sports, here I was, an inadequate frail boy dressing in dainty ladies things. Oh how shameful, how utterly shameful! I sat for minutes on end, almost in tears. I stood slowly, afraid I might faint. I considered undressing, ridding myself of the disgraceful garments and the shame, but when I stood in front of the dressing mirror, a solemn stillness came over me as a vision of feminine loveliness stared back at me in the mirror. I was transported into another world, a world meant for me. A slight movement to and fro brought on a stunning creaming, causing me to cry out loudly. The linen towel wasn‘t enough to protect the panties, and I had to hand-wash them later. After I had creamed, I swore I‘d never, ever crossdress again. And I didn‘t - until later that afternoon in an oatmeal colored sweater dress, and that evening, in a plethora of panties and petticoats, a silk chemise an embroidered satin bed jacket.


I was spent by the time Sunday afternoon rolled around, when Mimi was coming over to check on me and fix me dinner. I had to remove all evidence that I had been into my mother‘s things, putting everything back in its proper place.

After Mimi arrived, she went upstairs for some reason. When she came back down, she asked "Dahl? Did you notice that your mother left a very lovely evening gown behind? It‘s on her bed."

"Uh… no" I lied.

"Really? Well, perhaps later tonight you can have a look" she replied somewhat coyly. I shrugged my shoulders as if I could care less.

"You know, you and your mother are probably the same size" she continued.

’Where is she going with this? I thought. "Whatever…" I replied, again shrugging my shoulders, trying to sound insulted.

The next thing she said left me blushing: "Well, I was just thinking that you‘d look really cute in that gown." Her tone was non-committal, as if it was just a passing thought, so I didn‘t respond immediately or forcefully.

"You‘re blushing, aren‘t you Dahl?

"Huh?" I replied.

"You‘re blushing because I suggested that you‘d look cute dressed up in the gown?" she asked.

"Huh? No… I mean yes…" I stammered, trying to figure out the right response.

"It‘s alright, Dahl. Don‘t worry; I understand" she said, almost ending the conversation until she added as she turned to go into the kitchen: "But I know you‘d be a really pretty girl."

I tried not to think about what she had said and what she meant by "I understand". I wasn‘t going to pursue it with her.

Mimi left after dinner and I bounded upstairs to find that she had rearranged the gown on the bed. I dressed in it again and didn‘t get to sleep until late.

Mimi drove me to and from school on Monday and noted that I looked tired. She stayed overnight. My mother returned the next evening. Although I had tried my best to not leave any evidence behind, I doubted that I was successful. But mother never mentioned anything, and didn‘t ask why the gown was rearranged on her bed.


Chapter Three — The Redecorated Guestroom

A few days after mother returned from her trip, she enthusiastically declared that she was going to redecorate the guestroom across the hall from me. My room and the guestroom were at one end of a long hallway, while her room and my stepfather‘s room were at the other end, with the staircase in between. We had a big house, and the distance between our rooms was substantial, so I enjoyed quite a bit of privacy. The guestroom was, to that point, boring, containing a couple of twin beds and serviceable furniture, certainly nothing like the fine antiques that mother collected and showcased in other parts of the house. This was the last room to get her touch.

A few weeks after summer vacation had started, she finished redecorating, turning the guestroom into a very feminine chamber. The walls were papered with a floral pattern, pastel shades of pinks and blues against a cream background. The two beds were replaced with a mahogany four poster queen bed. The bed covering was a delicate wisteria satin quilt with a cream chenille throw folded at the bottom. The sheets and pillowcases were fine Egyptian cotton with ecru lace trim. At its foot was an antique mahogany loveseat with mother-of-pearl and exotic wood inlay on the back, upholstered with silver silk brocade with matching tasseled bolster pillows. The carpet was replaced with thick and plush wool in a cream that matched the wallpaper. She replaced the old bureau with a mahogany antique that went well with the bed and loveseat. An oval cheval mirror stood in the corner. But the crowning touch was a vanity dressing table that matched the loveseat — mahogany with inlays on the four drawers, a large round mirror, and a vanity slipper chair with the same silver silk brocade as the loveseat. The vanity mirror was antique silvered glass and had developed a patina around the edge. The vanity had two lamps with tasseled lampshades. On the bureau, mother placed a porcelain figurine by Armani titled ’Ada‘. To complete the redecoration, mother added a nightstand and two matching wingback chairs upholstered in velvet to match the comforter, with a small table between them. A gilt-framed mirror was hung on the wall between the two chairs and reflected the bed. More table lamps with tasseled shades sat on the nightstands on each side of the bed. When lit in the evening, the table lamps gave a soft romantic glow to the room. In the attached bathroom, she continued with the wallpaper from the bedroom and purchased coordinating plush velour towels.

When she was done, she couldn‘t resist giving me a tour and asking my opinion. I cordially praised her decorating skills, trying to hide how thrilled I was to have such a feminine chamber right across the hall from me. I don‘t think she ever showed it to my stepfather.

Mother had just finished redecorating when we went for our annual visit to her sister Beverley.


Chapter Four — My Favorite Auntie

Aunt Beverley lived in the hills above Larkspur in the San Francisco Bay Area. I loved going there, especially into San Francisco proper, and liked the openness of the city. We usually stayed with Auntie for ten days or so over two weekends. Auntie was well off, as my mother‘s family was quite wealthy. Aunt Beverly, being my mother‘s half-sister, did not have Oriental blood — she was all Scandinavian — tall, robust, and classically handsome blond, but she had recently taken to dying her hair pure white that gave her the most dramatic and mythical look imaginable. She liked to dress in hour-glass shaped vintage dresses and suits from the forties and fifties, and had quite a style and look about her. She would alternate between solid color suits and glorious floral and botanical print surplice bodice dresses. I loved being around her; she was so warm and friendly to me, and we just seemed to connect somehow. Auntie insisted on calling me by my given name, Evelyn.

Auntie had university degrees in psychology, and had written a couple of books on sex therapy along with another woman. I had seen copies of the books at her house. Mother tried to keep me in the dark about Auntie‘s books and expertise, but, being curious, I was able to learn a little about them. One book was called "Embracing your Sexuality" which, I gathered from brief glances, was about coming to terms with your sexual needs and satisfying those needs. The other book was called "The Orgasm Factor" and was all about how orgasms promoted mental and physical health, and in my furtive glancing, found it had chapters about attaining orgasms through masturbation and intercourse. Auntie was also a bit of a local celebrity, giving lectures on subjects in her book and appearing on a popular local radio talk show. Most of her focus was on female sexuality, but she also discussed male sexuality, mostly in terms of how males repressed everything and couldn‘t come to terms with their feminine side. From what I could gather, she pitied men.

Auntie had a housemate, Suzanne, who was a tall and willowy girl with shoulder-length hair dyed with Henna. Suzanne usually dressed in flowing skirts and tunics made of faille or surah, usually soft earth-tone browns and tans, but also could go vintage in her look with full skirts with petticoats beneath. She often wore her hair in pigtails. I thought she was lovely and I liked her fashion sense. She was somewhat boisterous whereas Auntie had a quiet sternness, and spoke softly and deliberately. But both had a good sense of humor that was somewhat bawdy at times. They were both taller than me and I always felt a little intimidated by them, especially Auntie.

Auntie‘s house was nestled in a cool shady canyon. It was a big French provincial style house with a circular driveway set back from the street. The architecture and landscaping gave it a very formal and elegant look. The entryway was small with a large formal parlor to the left of the entryway dominated by an open curved staircase that flared at the bottom. The hallway at the top of the stairs was open a bit to the floor below, and led to five bedrooms. All but one of the bedrooms was large. I stayed in the smallest bedroom. One of the larger bedrooms was turned into a private office and study.

Auntie and Suzanne owned a shop called the "Gilded Lily". It was located about fifteen minutes from their house in an old two-story courtyard retail complex. The Gilded Lily was an eclectic place, full of stuff that Auntie, Suzanne, and their associates, Penelope and Julie, had gathered from estate sales as well as retail and consignment items. There was antique furniture, such as dressing tables, armoires, beds, writing desks, dressing mirrors, settees, slipper chairs, lamps, and so on. There was also a large assortment of retail goods: bath oils and powders, scented sachets and paper to line drawers, towels and bathrobes, fancy stationary, cards, and writing supplies, wrapping paper and ribbons, silk flowers and chocolates, and a large selection of decorating pillows. The upstairs loft, half retail space and half office space, contained clothing — a good but modest selection of vintage dresses, jewelry, accessories, and lingerie.

I got to know Penelope and Julie a bit. Julie was in her early forties, a classy statuesque blond, with hair that arched and flowed around her face and touched her shoulders. (I discovered later that she was a trophy wife when she was younger — like my mother — but it had all ended in a bitter divorce.) She was a southerner and spoke with a soft accent, and was always nice to me. Penelope was younger than Julie and was ’pleasingly plump‘ with an easy smile that showed her cute dimples. Both Penelope and Julie were sweet, friendly women, well-groomed and feminine, and Julie, in particular, quite pretty. Auntie, Suzanne, Penelope, and Julie were all part owners in the shop, and they all dressed very nicely to lend an air of formality and professionalism to the business. They would come and go from the shop depending on what leads and purchases they could make.

The other shops in the complex were a mixture of things; over half were small private businesses — lawyers and accountants and such — while the remainder was uninteresting retail shops and cafes. Both Auntie and Suzanne had unkind words for the owner of the complex and all sorts of ideas on how they‘d transform it into something chic and upscale by giving the entire complex a facelift and kicking out most of the tenets, replacing them with ones who met their tastes.


Chapter Five — A Favor For Aunt Beverley

On our visit to Auntie‘s, mother took off overnight to visit an old friend in San Jose who was flying into the city for business. She left early in the day, leaving me to hang around the house with Auntie and Suzanne. I sat around watching television in the morning while Auntie and Suzanne were doing something upstairs. When they came downstairs, they both had changed out of their morning clothes (slacks and sweaters) into rather nice dresses; Suzanne in a toffee color broomstick skirt and teal tunic and Auntie into a dark blue pleated wool skirt and a crisp white cotton blouse with wide lapels. I wondered why they were so nicely dressed and just figured they were going out. But they stayed and fixed lunch.

While we were eating lunch, Auntie asked "Evelyn, would you do me a big favor?"

"Sure, I replied" thinking that she wanted me to move some furniture or help her with something heavy.

"Well" she started, "this is kind of awkward. You see, I got this call the other day from a lady looking for a bridal gown — not just any bridal gown, mind you, but a gown from a particular designer — Susan Lane — that has gone out of business. She heard about the Gilded Lily and how we collect dresses and such from estate sales. She offered a lot of money for a size eight Susan Lane original in perfect condition, and we found one a couple of days ago. But she wants detailed pictures. I guess we could go to the shop and dress one of the mannequins, but that‘s too much like work and besides, it‘s hard to get a decent picture from a mannequin — you can‘t just tell them to raise their arm or turn just so. Neither Suzanne nor I are a size eight, but we think that you might be — perhaps between a size six and eight, actually. So, I was wondering if you could do us a big favor and model the dress while we snap a couple of photos for this lady. It won‘t take long. It‘ll be fun. You know, with your long hair and a bit of makeup and padding, she‘ll have no idea that it‘s a boy modeling the dress."

I stammered something, objected, blushed, and tried to hide my inner excitement at the thought of being dressed in a bridal gown by Auntie and Suzanne. "Please, dear, don‘t be such a baby. It won‘t hurt a bit" she replied to my objections. I finally agreed. They followed me upstairs and Auntie asked me to shower and wash my hair. "We‘ll want to do something with your hair, OK?" she said. While I was showering, she knocked on the bathroom door, stuck her head inside and told me that she left some underwear on the bed for me, along with a robe.

When I came out of the shower, there was a white terry bathrobe that had the name of a spa embroidered on its pocket, an old-style white long-line side-zipper girdle with clasps for stockings, and a pair of pink satin pantie briefs decorated with a white lace panel down the sides.

"Everything OK in there, sweetie?" asked Auntie from the hallway.

"Do you want me to put these on?" I asked, sounding incredulous, but secretly wishing it was so.

"Well, of course, dear, you‘ll need something modest underneath and you need something to hold up the stockings" she replied matter-of-factly. "And the girdle will tuck in your waist. You need to have something on beneath the girdle and that‘s what the panties are for."

Nervously, I put on the panties and then the girdle. Normally, I would have been delighted to wear such undergarments, but not today — I was just so afraid to let on that I enjoyed dressing up in ladies things. The girdle was tight and did, in fact, smooth out my tummy and give me a bit of an hourglass shape. After tying the robe, I exited my room to find Auntie waiting in the hallway. "Let‘s go to Suzanne‘s room, dear. She‘ll do your hair".

When I entered her bedroom, I saw the gown draped across her bed. It was indescribably feminine. I expected a white satin wedding gown with a long train, but this was a floor length gown in an utterly romantic Victorian theme, décolleté with cascades of white and pink lace, a dotted net modesty panel beneath the décolleté, mutton sleeves with long lace cuffs, an empire waist tied with a long gold duchess silk ribbon, and the skirt alternating between white satin and lace panels. I think I must have gasped.

"Isn‘t it just so pretty?" asked Suzanne. "These Susan Lane ’Country Elegance‘ gowns are just treasures, and it‘s no wonder this lady is willing to pay a lot. And this one could be worn as a formal, or to a garden party, not just as a bridal gown."

Suzanne had me sit at her dressing table and she began to blow-dry my hair, brushing it out to give it volume. Suzanne had been a hairdresser at one point, and it showed as she expertly brushed and dried my hair. "You have such gorgeous hair, Evelyn! I was thinking I‘d have to use some gel to give it volume, but obviously not."

As Auntie watched, Suzanne applied makeup; some foundation cream, mascara, eyeshadow, blush, and lipstick. She used two different tones of foundation cream; a darker shade for my neck, Adam‘s apple and jaw-line, and a lighter shade for the rest. She stepped back to admire her work. Auntie exclaimed "My goodness, Evelyn, but you make such a pretty girl!"

"We need a bra and some padding, stockings, and then a full slip" said Suzanne, who was now enthusiastically taking charge of the transformation.

"Oh, do you know which bra I‘m thinking of Suzanne?" asked Auntie. Suzanne said she did, and she retrieved a white satin full cup with pink lace accents from her bureau. I sat at the dressing table, stunned, trying desperately not to let on how exciting it all was — I was being dressed by two attractive and vivacious women who were obviously enjoying themselves and the transformation that was taking place. Auntie helped me out of the robe and Suzanne helped me into the brassiere. For padding, Suzanne had produced two scented sachets, stuffing one in each cup. White stockings came next. Auntie remarked that she thought I‘d have to wear opaque stockings, but since I had hardly any hair on my legs, I could wear something sheer. Suzanne rolled up a stocking and helped me insert my foot. Without thinking, I began unrolling the stocking up my leg and fixed it to the clasps on the girdle.

"It seems you‘ve done this before" said Auntie. I stammered something about it being easy enough to figure out. I don‘t know if she believed me, but nothing more was mentioned as I rolled the other stocking up my leg and fastened it.

After donning the stockings, Suzanne went to her closet, saying "I think I have a long negligee that might fit you." She retrieved a most feminine white satin negligee with pink lace trim at the bodice and hem, matching the brassiere almost perfectly. She and Auntie both helped me into it, raising it over my head and carefully drawing it over my coiffed hair and avoiding my makeup. I stood as Auntie smoothed it over me, tugging the hem to get the fit just right.

"Oh wow!" they both exclaimed as they stood back, looking me from head-to-toe. "Just look at you, Evelyn! My goodness gracious: if you ever have a need to disguise yourself, just put on some makeup and a dress." She turned me around to look at myself in the full-length mirror. I could barely look at my reflection. My trepidation, silence, blushing, and furtive glances were probably as telling as blurting out "I‘m a crossdresser". Auntie and Suzanne exchanged a knowing smile.

"Now, let‘s get you into that dress, dear. I can‘t wait to see you in it" said Auntie in a velvety voice. The dress buttoned in the back with a couple of dozen small satin covered buttons. They helped me step into it and guided my arms into the lovely lace sleeves. Auntie stepped back to watch Suzanne button me up, while I watched in the full-length mirror. It took several minutes to do all the buttons. I could barely talk above a whisper, and tried to make a joke or two, but ended up making the situation even more embarrassing for me. The gown fit well enough although it was a bit large.

"Oh my goodness" breathed Auntie when Suzanne had finished buttoning me. "Suzanne, can you believe just how pretty he is?"

"We need some pearls and a big pretty hair bow" said Suzanne, and she began to look through the drawers of her bureau. She produced a four-strand faux pearl necklace, matching bracelet, and pearl drop earrings. The earrings had posts, meant for pierced ears, which mine were not. Auntie solved the problem by cutting a flesh-colored band-aid and wrapping it around my earlobe, leaving a little flap protruding off the bottom of my earlobe. She then poked the earring through the flap. It was quite a clever trick. While Auntie was dealing with the earrings, Suzanne went looking for a hair bow, finding a big white satin bow with long wide ribbon streamers. "Remember this Beverley?" she asked, holding it up. Auntie gave a little giggle — it was some sort of private joke. Suzanne gathered my long hair in the back and held it while Auntie fixed the hair bow.

"We need some heels, too" said Auntie, "We can‘t have the hem dragging on the floor. What about those white dress sandals of yours, Suzanne?" A few moments later, I was sitting down while Suzanne helped me into the impossibly high heeled flirty sandals. The heels fit well — in fact, they might have been a bit big. Both Auntie and Suzanne remarked on this, saying they were surprised how small my feet were and how easily they fit the heels. They helped me stand, thinking that I‘d have all sorts of issues with wearing heels, and when I didn‘t, Auntie said quietly "Well look at that — you‘re a natural in heels."

"One last thing" said Suzanne, and she went to her bureau and came back with a pair of white lace gloves. "Brides wear gloves, so you should too" she said. Each glove had a little satin rose with blush pink ribbon accents on the back of the hand.

They both stepped back for an inspection as I looked at myself in the mirror. I was deeply embarrassed, for my reflection showed just how feminine I looked, how feminine I felt on the inside. Under different circumstances, I would have been utterly overcome with sensual pleasure, but I knew I had to hide my feelings from them. Auntie let out a deep sigh and said in a whisper "Just look at you. Oh my goodness, just look at you. You are just ravishing."

The trance was broken a few moments later when Auntie blurted out enthusiastically "Where‘s the camera? We need pictures!"

She took a few pictures with her digital camera, but the light was too low and the flash was washing everything out. "Let‘s go outside in the garden" suggested Suzanne. I thought about it for a second or two — going outside dressed! But the garden was enclosed and no one would see us.

I slowly descended the staircase, holding up the hem of the gown so as not to trip. Auntie and Suzanne were very concerned that I might trip on my heels, so they stayed close to me. As I took each step carefully, I began to feel flush and I let my guard down for a few moments, and I think I let out a sigh and detected a smile from Auntie and Suzanne.

When we reached the bottom floor, Auntie said "You know, Suzanne, Evelyn here is just too tense to take a decent picture. What do you say we sit in the den for a while and let her — excuse me — him — have a glass of sherry?"

And so I sat on the couch, dressed in an utterly feminine bridal gown; made up, wearing expensive pearl jewelry, my long hair coiffed and tied back with a big girlish hair bow, sipping sherry, while Auntie and Suzanne sat opposite me, casting admiring glances at me and my dressing. "You know, Evelyn, you are such a beauty in that gown. Promise me you‘ll have some fun posing outside" said Auntie.

The sherry helped me relax, and when we stepped outside to the rose garden, I felt the lady inside of me coming out. They had me strike various poses, Auntie pleading with me to give a nice smile. They took close-ups of the gown to show what excellent condition it was in. Suzanne wanted to freshen my makeup for the lighting conditions, and she retrieved the powders and lipsticks, brought them outside, and had me sit while she freshened me. Then it was back to posing for the camera. Once or twice I let myself go and gave a coy, knowing smile and posed myself in a most ladylike manner, which elicited oohs and ahhs from Auntie and Suzanne, which made me blush and withdraw.

The photographing was declared finished after a good half-hour and we went back inside for some tea. As the tea was being made, I excused myself to use the toilet. Auntie gave me a bit of advice, telling me how to hold the skirt while sitting on the toilet. Alone in the downstairs bathroom, with its big mirror, I felt faint as I undressed. A real boy would have objected and refused to do what Auntie and Suzanne had requested. A real boy would have taken command of the situation. Then again, a real boy wouldn‘t look so pretty. My whole demeanor — my quietness, my blushing, and my furtive poses — was all positive proof that I was deeply affected by the dressing. A real boy wouldn‘t be as stimulated as I was, either, sitting on the toilet, having difficulty passing water because my daintie was so stimulated. I took longer than I should have to get out of the toilet, but no mention was made as I returned to the kitchen for tea.

We had a leisurely tea — almost an hour. Auntie and Suzanne talked about goings-on at the Gilded Lily, discussed the rest of our vacation, and asked me about school and such. Auntie asked about Mimi, as they had met a couple of times when Auntie came to visit us. Whenever I tried to act like I wasn‘t enjoying being so exquisitely dressed, they‘d compliment me on how pretty I was. Suzanne even asked if I ever dressed-up at home ("Of course not!" I exclaimed). It got to the point where I just sat blushing, reveling in the way I was dressed.


It was getting on to late afternoon and it was time to start preparing dinner. "I‘d love for you to eat dinner with us while dressed up in a nice dress, Evelyn — just not that one; we can‘t let anything spill on it."

I made my objections, saying how I wanted to change back into my jeans and T-shirt. Auntie said "Oh, don‘t disappoint us dear. It would be so much fun for us if you‘d wear a nice dinner dress. Suzanne? You know that blue dress of yours? That one that‘s too small? Don‘t you think Evelyn would look fantastic in it?"

"She… Oh, excuse me, Evelyn! He really would" said Suzanne with immense enthusiasm.

I whined and complained. It was just too much — didn‘t they understand how they were torturing me? I was completely torn apart by trying to be a boy and, at the same time, reveling in the experience. Finally, Auntie put her foot down, saying "Evelyn, can‘t you do this for Suzanne and me? We‘re so enjoying this, it doesn‘t hurt, and it beats the hell out of the alternative of just sitting around as couch potato watching television. Now, if you don‘t want to play along, well…" her voice lowered "…I guess I could show your mother the pictures of you in the bridal gown…"

That threat did it. I acquiesced.

"Then it‘s decided" replied Auntie gaily, clapping her hands. "Let‘s get you out of that gown and into your dinner dress."

Suzanne led me back upstairs to her room. Auntie stayed behind to finish preparing a casserole and put it in the oven. Suzanne helped me out of the gown, gloves, heels, and jewelry and carefully put the gown away in her closet. As I stood in the negligee, she retrieved a blue dress from the closet.

She held it up for me to see. It was a simple and classic dress in powder blue georgette. The bodice had a modest and clean V neckline. The sleeves were long and oh-so-billowy, made of sheer powder blue chiffon and ending in long three-button cuffs. The neckline was trimmed with two narrow overlapping ribbons of chiffon that matched the sleeves. The waist had a two and a half inch matching fabric belt with a fabric covered buckle. But the skirt — oh my, the skirt —intermission length with one-inch box pleats, metallic thread woven into the georgette to give it a sparkle. The dress zipped in the back and came with a full slip made of high luster white satin, which would reflect light back to the skirt to show off its sparkle.

"Isn‘t it pretty?" she asked. "It really catches the light — you‘ll see. Too bad it‘s too small for me because I really like it. It should fit you just fine."

She laid the dress on her bed. The phone rang (scaring the hell out of me) and Auntie answered downstairs. I must have been trembling, for Suzanne said "Why so nervous, sweetie? I‘m not going to hurt you, for goodness sake! Every boy needs to be dressed up as a pretty girl at least once; and some boys much more often than that. Heck, in San Francisco I bet there are boys being dressed up every day. Now, I bet you‘re sick of wearing that girdle. I know I would be! Let me see…" she turned and began looking through her bureau drawers, letting her last comment about boys dressing up hang in the air.

"Here they are" she said. She pulled out a wide garter belt and pantie brief that matched the brassiere; white satin with pink lace accents. My heart skipped a beat when I saw these luscious underthings. She put the garter belt and pantie brief on top of her bureau then looked back in the drawer, musing to herself "well, I totally forgot about these". She pulled out a pair of roomy white tap panties with a pink Alencon lace appliqué on the sides. She put this on top of the bureau as well.

"Now, you sit down and take off your stockings and then the girdle while I look for some heels to go with the dress, and maybe some different stockings. I think I have a scarf to go with, too."

I did as she said, unclasping the stockings and unrolling them. Then I stood and reached beneath my negligee and unzipped and removed the girdle, leaving on the pink satin panties. Suzanne has found shoes for me; powder blue T-strap sandals with high stiletto heels. When she saw I had removed the girdle, she brought the pantie briefs over to me and said simply "Here, slip this on, okay?"

I was relieved to discover that the fabric of the pantie briefs had a bit of spandex and fit nice and snug — maybe it would hide my excited daintie. I wore them over the pink satin panties.

Suzanne had now found a powder blue chiffon thin rectangular scarf. "Hmm…" she said to herself and then, turning to me, said "We could use this as either a long tie worn around your neck or as a hair tie. We‘ll experiment and see what looks best."

Finally, she retrieved a pair of almost nude stockings that had a bit of metallic sheen to them.

"Okay, sweetie, off with that negligee and I‘ll help you into the garter belt."

I did as she said, and stood blushing deeply (how much more blushing could I do in one day? I thought), my ears ringing. I was facing the mirror on the dressing table when she wrapped the garter belt around my waist and clasped the back.

"You‘re so skinny that this garter belt doesn‘t even fit you!" she said with a giggle. "Let me see if a safety pin will help." She fetched a safety pin and gathered some of the loose material in the back and pinned it. "There, that helps. Does it fit better now, sweetie?"

"Yes, I guess so" I replied breathlessly.

"Stockings next!" she said gleefully. "You know what to do."

I rolled up the stockings and attached them to the garter suspenders, working quickly, not wanting to let on how much I loved drawing on stockings. Suzanne hummed quietly to herself as she watched me. I fumbled with the garter suspenders and finally managed to get both stockings clasped.

"Why don‘t you go ahead and wear these as well?" she asked, holding up the white tap panties. "The fabric of the slip that goes with the dress is really delicate and might get hung up on the hooks or the safety pin on the garter belt, and these panties should cover them" she offered as an excuse. It didn‘t make much sense, really, but it was enough of an excuse to get me into them. I stepped into them and drew them up as she watched. When they were in place, she said "My goodness, but you are so cute! Just remember, dear, life‘s too short for boring underwear!" The fact that the panties didn‘t cover the back of the garter belt went unnoticed.

"And now the slip, sweetie; arms up." She guided the slip over my head and pulled it down. I let out a little sigh of relief for my foundations were now hidden out of view.

A minute later, Auntie knocked on the door and entered. "How‘s it going in here you two? How much fun have I missed?" she asked with a smile. She told me that the phone call was from my mother ("Don‘t worry dear, I didn‘t tell her about our day" she added quickly). She confirmed that mother would be spending the night in the city which was a relief to me — the last thing I wanted was my mother showing up unexpectedly and finding me all dressed-up.

While Auntie and Suzanne watched, I stepped into the dress and Auntie zipped it up. I tried not to admire myself in the mirror, but my furtive glances told me that, indeed, the dress was exquisite. The delicious fabric of the skirt caught the light and just glowed and shimmered; with each motion I took it seemed to be alive, the pleats opening and closing to give it a graceful and flowing movement, catching the light to make the skirt shimmer even more. The slip showed beneath the bodice and I found myself wishing the slip was adorned with lace to show from beneath the georgette. The dress was a bit big for me, but the cut was such that it didn‘t make much difference. After cinching the belt as tight as it would go, it fit well enough.

The sleeve cuffs needed buttoning, and I stood facing myself in the mirror as Auntie buttoned one cuff and Suzanne buttoned the other. With their heads down, I had a private moment of self-awareness in the mirror, just a heartbeat or two; the scene was just too surreal and sensuous, and I let out a silent ’Oh‘, my painted lips parting seductively. They had me step back and walk around a bit, giving comments on how lovely and graceful I was in the dress.

I sat at the dressing table again. Suzanne went to work with silver and blue eyeshadow and more mascara, really lengthening and darkening my lashes. Purplish lipstick followed along with darker cheek blush. She was really tarting me up.

Auntie was standing behind me, watching my reflection in the mirror as Suzanne applied the makeup. "I was telling Evelyn" began Suzanne, addressing Auntie, "that every boy needs to be dressed up as a pretty girl at least once."

Auntie gently placed her hands on my shoulders and looked at me in the mirror, right into my eyes, and said "Oh, most definitely… At least once; some boys need to be dressed much, much more often than that… like, every day." She let the comment hang in the air, her hands still gently on my shoulders, as Suzanne concentrated on my makeup.


I felt humiliated. Why were Auntie and Suzanne doing this to me? Were they trying to humiliate me? Or were they doing it because they thought I enjoyed it? Or was it because they enjoyed dressing me? Wearing the bridal gown was quite enough, but at least there was an excuse — they wanted pictures. Part of me wanted desperately to stop, to throw a tantrum and get back to being a boy. But the other part of me — the part that was reveling in the situation, was just as compelling. Torn between two worlds, I just sat there as Suzanne finished my makeup.


The chiffon scarf was looped around my neck and tied in front with a loose knot. They didn‘t like it, so Auntie retied it so that it formed a kind of flower petal on the side of my neck. They didn‘t like that either, so it was looped around my neck and tied in the back, creating sort of a choker, the streamers falling down my back. "Hmm… I like this" said Auntie. "It hides that little Adam‘s apple of yours." That comment stung me a little bit, for I had wished at times that my Adam‘s apple would just disappear altogether.

Earrings came next; we tried gold, but settled on multiple strands of long delicate silver chains. We experimented with lots of different necklaces, finally deciding that all of them distracted from the clean elegant lines of the bodice.

Suzanne selected an antique filigreed silver hairpiece that had a polished grayish silver stone set in the middle. She took strands of hair from my temple and clasped them together high up on my head with the hairpiece.

Finally, I put on the heels. The T-strap sandals matched the delicate dress and gave really gave it a flirty look.

"Oh my… oh my" whispered Auntie. "You‘re just so… so pretty Evelyn! Come, let‘s go downstairs and get a few more pictures in before dinner."

We went to the staircase together, but Auntie insisted that she and Suzanne go down the stairs first so they could watch as I came down. "Be very careful on your heels dear" said Auntie as I began my descent. About halfway down, they had me stop so they could get the camera and take pictures because, as Suzanne said, "You just can‘t believe how elegant you look coming down those stairs."

After more poses and pictures, Auntie and Suzanne set the table, leaving me alone in the parlor to evaluate myself in large mirror hanging on the wall. My feminine side won out and I became infatuated with the movement of the skirt and the utter femininity of the dress. It was definitely a dramatic special occasion dress that seemed perfect for wearing on the dance floor. In this regard, it was a dress for a vivacious woman on a date. But it also was reminiscent of a dress a young girl might wear to a party. One moment, I was that vivacious woman on the dance floor. The next, I was a little princess playing dress-up for a party. My primping and posing in the soft afternoon light was so titillating that I had to stop.


Thankfully, dinner was light and easy — I just picked at my food — and our conversation was about politics and not about me and my dressing. After dinner, we did a little clean-up and Auntie announced "Do you know what would be fun? If we three ladies took a drive up to Lookout Point." I think my heart skipped three beats and I felt faint.

"Auntie, there‘s no way I‘m going out dressed like this!" I almost screamed.

"Nonsense dear: why not?"

"Someone will see me, that‘s why!" I exclaimed.

"But sweetie, nobody here knows who you are. Anyone that sees you will think you‘re just a pretty girl in a lovely dress" was her rejoinder.

"But we could get in an accident or something" I replied in a pleading voice.

"Oh, pshaw; I‘m a fine driver — unlike your mother — and it‘s an easy safe drive to Lookout Point. We‘ll be fine. I‘ll drive nice and slow and extra cautiously if that‘ll make you feel better. Besides, this will be something you‘ll always remember and can learn from."

Her last comment struck me as odd, but then again, the whole day had been extraordinary.

I was out of excuses. Deep down inside, I did want to go out — it would be the thrill of a lifetime! We‘d go to Lookout Point, watch the sunset from the car, nobody would notice me, and we‘d be home soon. I let out a big sigh, saying "Okay, if it makes you feel better, I‘ll go."

"Great! Suzanne? I think you and I should dress up a bit ourselves to make Evelyn feel more comfortable, don‘t you think? And we should get you a purse, Evelyn. Suzanne? Do you have a purse that Evelyn can borrow? I don‘t think I have one that‘ll go with that dress" inquired Auntie.

They both scampered upstairs, almost giggling, leaving alone again in the parlor. I now had a bit of time to myself and I let myself go and primped and posed in the mirror. I minced to the bathroom and had too much fun undressing to use the toilet and again had to force myself to relax before I could pass water. My daintie became very stimulated as I drew on the panties. In such a state, my panties — Suzanne‘s panties — would become sullied. I looked around for something, anything, which might serve as a napkin to absorb the little beads of cream my daintie was oozing. One of the drawers contained a stack of linen hand towels, and I took one from the bottom, cut it in half with a pair of cuticle scissors, and used it as a napkin beneath my panties. I would deal with the other half later.

I exited the bathroom and spent a few more minutes alone with the mirror in the parlor. Then Auntie and Suzanne descended the staircase. They looked fabulous. Auntie had changed into a long black rayon skirt and a white silk side-wrap blouse with a dramatic ruffled portrait collar. She wore a chunky purple, blue, and white stone necklace that really set off her ensemble and her hair. She had done her makeup, too. She was beautiful. Suzanne had changed into a matched two-piece scarf dress, the abstract window shade pattern made of hues of brown, teal, blue, and a bit of red. The skirt and tunic top had asymmetric hemlines. She wore no jewelry and didn‘t need any. Like Auntie, she had done her makeup. Both of them wore high heels, Auntie in black pumps, Suzanne in brown stiletto sandals. Suzanne was holding two purses.

I complimented them, saying they both really looked beautiful. "Not as beautiful as you, dear" replied Auntie.

Suzanne handed me a rectangular white clutch purse. I could tell by its heft that it contained some cosmetics. Suzanne offered that she had put some makeup in it "In case you need to freshen up" she said with a wink.

"All set?" asked Auntie.

I sat in the back of Auntie‘s big Cadillac — I felt a little more hidden there than I would be in the front seat. They both stood outside the car door giving me tips on how to get into the car without mussing my skirt.


Lookout Point was a fifteen minute drive, but it seemed like an eternity. I began to relax a little, and fondled and stroked the lovely skirt as I sat hidden in the back seat. When we arrived, there was one other car, but, much to my relief, it left, leaving the place to ourselves.

Auntie and Suzanne got out of the car. With my head buzzing with prospect of actually presenting myself to the world outside Auntie‘s house, I too stepped out as well. A cool breeze was blowing and it gently lapped at my skirt as I walked with Auntie and Suzanne to the guardrail and took in the sites of San Francisco in the distance. The sun hadn‘t quite set yet and we watched the last remnants of the day disappear below the horizon. It was an idyllic scene, peaceful and spiritual. I was doing it — going out as a lady — and it felt so wonderful, so right. My mood became such that if Auntie or Suzanne had asked, I would have told them all my secrets; that I was thrilled to my core to be wearing such a pretty dress, that I dressed up whenever I could at home, that my dream was to be, as Auntie said, a boy who was dressed up as girl every day.

We walked along the paved path beside the guardrail to another point. The cool breeze felt wonderful as it played with my skirt. We were now uncomfortably far away from the car, at least in my paranoid mind. Sure enough, another car pulled up, its headlights shining directly on us for a moment or two, and parked between us and our car. There were two couples in the car. They stayed in their car for a few minutes.

"We should get going" said Auntie. "Evelyn, you must be tired; after all, you‘re still on East Coast time, aren‘t you?"

I agreed. I was really enjoying myself, but the visitors unnerved me. As we began to walk back to our car, the other visitors exited theirs. They stood at the guardrail in front of their car. Auntie confidently strode past them on the walkway and I followed, Suzanne behind me. Someone said "Good evening" and Auntie replied "Lovely out tonight, isn‘t it?" A few more pleasantries were exchanged as we walked past, my head down, trying not to be noticed. But I was noticed, for as we passed them a few steps, I distinctly heard one of the women say "pretty dress…"

Back in the car, we drove back into town. "We need milk and yogurt" said Suzanne. "Let‘s stop off at the dairy market". We pulled up to a small market and parked.

"Want to come in Evelyn?" asked Auntie with a grin, teasing me, knowing that I‘d refuse.

"Uh… no thank you Auntie" I replied with a smile.

"Okay, sweetie, just wait here and we‘ll be back in a couple of minutes."

While they were inside, I opened the purse and couldn‘t resist touching up my lips with the tube Suzanne put in the purse. Then a bit of cheek blush. There I was, sitting in the car, wearing a fabulous dress, touching up my makeup, just as a lady should.


Back at Auntie‘s house, sherry was poured and Auntie and Suzanne toasted me on a wonderful day. I let out a little yawn.

"You must be sleepy dear. Go ahead and go to bed. You can get undressed by yourself, I assume? Just leave everything in your room and we‘ll just put it all away in the morning. Suzanne and I are going to watch a little television."

Both Suzanne and Auntie gave me kisses on the cheek and thanked me for a wonderful day. Then Auntie blurted out: "Drat! Evelyn, I took the sheets off your bed and washed them, but they never made it to the dryer. Oh well. Why don‘t you sleep in your mother‘s room tonight?"

"Uh… okay" I replied. The guestroom that mother stayed in was much nicer than the small one in which I slept. Not only that, but the closet doors were mirrored.

After a few more goodnights, I ascended the staircase to the room where mother was staying. I entered the room, shut and locked the door, and let out a huge sigh, for I was finally alone. I just wanted to admire myself in the closet door mirrors.

That‘s when I noticed the negligee on the bed; the very one I had worn beneath the bridal gown. Auntie or Suzanne placed it there. On top was a handwritten note that said:

Dear Evelyn:

We‘ve had so much fun today. You make such a pretty girl. We thought you might like to end your day by sleeping in a nice nightgown.

Much love to our beautiful ’niece‘;

Auntie and Suzanne

I stared at the note and the negligee in disbelief. The first thing that struck me was the ruse Auntie played — she knew I‘d be spending the night in this room and not my own; there was no ’forgetting‘ to dry my clothes. The second thing that struck me was just what a wonderful evening this was going to be. It was barely nine o‘clock and I had several precious hours to play.

My first creaming was in the bathroom in front of the well-lit mirror. I was leaning against the countertop, a pillow strategically placed between my oh-so-stimulated daintie and the countertop. (I had found more protection for the pantie gushing that was most certainly going to occur.) I was a seething caldron of emotions, bouncing between shame, humiliation, pure joyful erotic pleasure, and questioning of Auntie‘s motives. Why had she done this to me? Why did I so want to be dressed as a girl? Why did I love dressing up as a girl? Why was it so very erotic? How did Auntie know? Did she dress me up for her enjoyment, for mine, or both?

I began to cry; tears ran past my mascara and down my cheeks. The precipice was reached; I gently bit the knuckle of my index finger and whimpered as wave after wave of cream gushed forth.

The first creaming settled my mind and thoughts. No feelings of utter shame arrived, nor were there any desires to undress from the shameful garments. My next creaming was less than an hour later as I sat in front of the mirrored closet doors, my panties at my ankles; the skirt held with one hand while the other held a soft velour hand towel and coaxed another stunning creaming. After that, I showered (it occurred to me that maybe Auntie and Suzanne would hear me showering and realize it was a couple of hours after I had gone to bed. What was I doing in the meantime? They would wonder and probably draw the correct conclusion.)

I slept in the negligee and foundations. I awoke early in the morning and had a splendid pillow ride and creaming, then fell asleep again. I got up late in the morning and gathered the dinner dress ensemble and negligee on the chair, a mound of dainty treasures. I had kept the note that Auntie and Suzanne had written me, folded tightly in my wallet, a souvenir of a fabulous day. I would probably destroy it later — I just couldn‘t risk anyone ever seeing it. I put the cut-up linen hand towel I had used as a pantie napkin in the trashcan in the bathroom, hiding it amongst the tissues and such.


I came downstairs in jeans and a T-shirt. Auntie and Suzanne were in the study. "Good morning, sleepyhead" said Auntie cheerfully. "Come in here, precious, there‘s something I want to show you." They had downloaded the pictures to their computer and beckoned me over to look.

I couldn‘t believe what I was seeing. Those weren‘t pictures of me; they were pictures of some very pretty young lady in an exquisite Victorian gown and a beautiful dinner dress. "You are just stunning, Evelyn!" cried Suzanne. "Your mother may be a professional model, but you… you just take the cake!" I feigned indifference, but I just couldn‘t take my eyes off of the photographs.

"Don‘t worry, dear" said Auntie "no one will see these but us and the lady that wants to buy the gown. Would you like me to copy the files for you?" she asked.

"No, no, no" I replied, although I secretly wanted them.

Suzanne made me a late breakfast. As I ate, she told me how special yesterday was and how she was kind of sorry mother was coming home today because, if she wasn‘t, we could do some more dressing up.

"No way" I said, trying to sound like a real boy and not the sissy that I was.

"Oh, I think otherwise" she said with a wink.

It wasn‘t long before mother returned everything went back to normal. But I did go to bed early that evening (I didn‘t sleep much the evening before) and read the note from Auntie and Suzanne before snuggling up to a pillow.


Chapter Six — A Belated Birthday Present

Before we left a few days later, Auntie and Suzanne offered me a job after graduation at the Gilded Lily. They knew that I had applied to go to Berkeley and if I was accepted, it would be a perfect opportunity to settle in. I was to graduate high school after the first semester — there were two only two easy classes that I needed to complete in order to graduate. I was a straight-A student, but because my earlier illness had made me skip a semester, I lacked the two classes. So if I was accepted at Berkeley, I could go out and work for Suzanne in the winter and spring, then attend summer orientation classes at Berkeley and start school in the fall. Mother wasn‘t too keen on the idea. She told me she was looking forward to having me around the house for the entire school year.

On the day we left, Auntie presented me with a gift, a belated birthday present, she said (I was a Gemini, of course). It was a set of pajamas and a robe of the highest quality white silk charmeuse with powder blue piping, with my initials in a florid blue monogram on the breast of the robe. The pajama top was double-breasted. They didn‘t look unquestionably feminine, but there was little doubt that these were ladies pajamas. The fabric was exquisite and definitely not something boys would wear, and the cut was for a lady‘s figure. Mother thought they were very nice and never questioned how feminine they were, but she did suggest later that my stepfather need not know about them, and that I might want to keep them in the guestroom closet.

"Ellen?" said Auntie, addressing my mother, "you know how we‘re getting more clothing at the shop? Well, some of the things coming in are really quite nice. I was thinking that I could set aside some of the nicer things and send them off to you. Would you like that?"

"Sure, why not?" she replied. "If they don‘t fit or I can‘t use them, I‘ll send them back at some point."


To be continued…

The Awakening of Evelyn - Book 2

Author: 

  • Evelyn D. Fairechild

Audience Rating: 

  • Adult Oriented (r21/a)

Publication: 

  • Novel Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

Other Keywords: 

  • lingerie
  • Petticoats
  • Soft Sweaters
  • Boudoir

Permission: 

  • Posted by author(s)

The Awakening of Evelyn

Book 2

Evelyn D. Fairechild


Upon returning from visiting his aunt, Evelyn is cosseted by his mother and her friend Mimi.



Chapter Seven — Return From Auntie‘s

When we returned from Auntie‘s, we discovered that my stepfather purchased a mansion in the Hamptons on Long Island. He didn‘t ask mother, apparently; he just did it. He said he had to move quickly on the purchase, and had gotten a great deal, paying cash. We knew it was on his mind; ever since he became wildly successful and rich, and both he and my mother wanted a showplace mansion. He was spending more and more time in New York, and it made sense that he‘d move closer to the city. We drove up the next weekend and took a tour. It was a big and elegant stonework mansion. It had two distinct wings, one facing south, the other facing north, and each with several rooms. Mother‘s thought was that she and my stepfather would take the south wing, and I could have the north wing. I didn‘t ask how much it cost, but it had to be millions. For myself, I really didn‘t care, for my thoughts were with moving out to the Bay Area — this would never be my home. I had grown up in Pennsylvania, and that‘s where my home really was. I resented my stepfather for wanting to move. But my stepfather had, at least, a modicum of civility, and said that we wouldn‘t move in until after I finished high school — late spring was the date that was worked out between my stepfather and the current owners. My mother made a comment that she‘d need to have a staff of maids to keep up with the place.

When we returned from the Hamptons, things settled down. There were several weeks left before school started. The incident with Auntie and Suzanne never receded from my mind. Although mother and I were close, there was no way I would tell her about the incident, or of my desires. I was still ashamed of them, I guess, and I felt that if I told her my desires, she‘d be devastated to know she raised her only son to be a sissy. She might even become angry and wouldn‘t let me go back to Auntie‘s or to school at Berkeley. Mother and Auntie had very different personalities; where Auntie was very open about sexuality, mother was not, at least around me. She was as private a person as I was. I would never expect her to dress me up like Auntie did.

But subtle changes began to occur.


One Thursday evening, my stepfather was in the city and it was just mother and me. After dinner, I was sitting around, bored, watching television, when mother appeared wearing her mint green nightgown and robe. It wasn‘t unusual for mother to wear one of her modest night dressings in the evening; she had many and liked to wear them. This particular one was made of a very nice synthetic blend (I had tried it on once and loved the feeling of the fabric). The robe had long sleeves with ruffled cuffs trimmed with white eyelet lace, as were the lapels of the robe. The peignoir, hidden beneath her robe, had an empire waist, and all the hems were trimmed with white eyelet lace as well.

Mother sat down to watch television. A movie she wanted to see was due in half an hour. She suggested that I go change into the pajamas and robe that Auntie had given me. To sweeten the proposal, she said she‘d let me have a glass of wine and we could watch the movie together. My mother approved of allowing teenagers to drink in moderation at home, thinking that it would prepare them better for adulthood. She got the idea from Mimi who, being French, thought that wine should be given to infants and family pets. Reluctantly, I did as she asked — I was both delighted to wear the set and mortified that my own mother would see me in it . I went the guestroom, retrieved the pajamas from the closet and changed into them. Mother complimented me, saying I looked really ’nice and comfortable‘ in the ’lovely set‘ and that I should wear the set as often as I wanted, adding the caveat that perhaps it would be best if my stepfather didn‘t see them. The movie was an old Hollywood black and white romantic comedy.


Mother got me a part-time job at the historical society‘s library and museum. Mother was the Treasurer for the historical society, which housed the library, located in an old building on the outskirts of town. It was a minimum-wage job, and I suspected that mother was donating the money to pay me. There was only one full-time curator, a nice older lady named Melanie. Melanie and mother had become friends, having met through the historical society. Melanie had been to our house several times, including for dinner. She and Mimi had hit it off as well. She was gregarious and fun and a self-described ’child of the sixties‘ and would entertain us with stories from the early days of the feminist movement. She was a little heavyset but still attractive with a disarming dimpled smile, and liked nice clothes — a bit incongruous given her personality — and always dressing nicely for work. Her husband had passed away several years before and she kept busy with the historical society, recently replacing the previous ancient curator. She was supported at the library by a couple of older volunteer docents who really didn‘t do much. The work itself was incredibly easy. The library had three floors, and Melanie took care of most everything on the ground floor where her office was, and charged me with shelving books on the upper floors. The second floor contained some reference books and dusty exhibits, and third floor contained historical documents from the town. All the popular material and exhibits were on the first floor. I liked the décor; there was an amusing mixture of Victorian furniture with lace doilies and a few tables with old reading lights.

I had a little office on the third floor; basically a storage room with a desk. There was an intercom phone so that Melanie could talk to me without having to come find me. There was a bathroom on the floor, only accessible through my little office.

Melanie had acquired a large collection of old and somewhat rare books that were to be housed on the third floor. My initial task was to shelve them all according to a classification Melanie had developed. The first day on the job I discovered just how empty the upper floors were. I was shelving books for an hour floor before anyone showed up; mother and Mimi. I heard the old clunky elevator well in advance of their arrival — it sounded like a freight train. I gave them a little tour. Several days passed before I had another visitor. At first, there was a lot of work to do, shelving the newly acquired collection. The agreement was that when I started school, I would work one day a week.

I was working late one afternoon and Melanie wanted to leave, so she showed me how to close up by setting the alarm with a code. Soon after, she entrusted me with a key to the building, suggesting that I could come in and work when the library was closed.

My job title was ’assistant librarian‘. My feminine side liked the idea of being a librarian — I could imagine myself as a shy and diffident young lady librarian, all prim and proper, dressed in tasteful Victorian themed fashions, blouses with lace band collars, my hair done up in a loose alluring Gibson-girl bun.


One afternoon, mother announced that she wanted me to take some extra vitamins and drink a special herbal tea. Apparently, she had read some article about the health benefits of this particular tea and decided I should go on a tea and vitamin kick. It wasn‘t unusual for her to start some new diet, and I learned to just let her try it out until she lost interest. We always had tea available and I liked regular black tea, but I wasn‘t too keen on herbal tea. This tea was a mixture of chamomile and other herbs and didn‘t taste particularly good, but over time (and with the addition of honey), I got used to it. I‘d still have coffee whenever I needed a jolt, but mother would insist that I‘d drink my ’special tea‘ every afternoon and before bed, and take the new vitamins with every meal.


As school approached, mother began buying my back-to-school wardrobe. The first things she purchased for me were not clothes but all sorts of shampoos, conditioners, soaps, and lotions. They would just appear in my bathroom, and mother would tell me later to give them a try. Eventually, my bathroom shelf became full of products; exfoliate facial scrubs and creams, body and hand lotions, and hand-made perfumed soaps. All the products were meant for women, and when I finally questioned her about them her response was that I was being silly; it didn‘t matter and I should use them — they would make me feel nice and clean. In fact, she seemed a little miffed that I had even asked her.

The back-to-school clothes she purchased for me took a definite turn to the soft and feminine. When she‘d take me out to buy clothes, I would choose the typical latest fashions in T-shirts, sweatshirts, and designer jeans, and she‘d try to steer me towards a softer look, but I always won out. But then she‘d go out on her own and return with soft sweaters and soft supple jeans, wool slacks, and corduroy slacks. They were all androgynous enough, but, taken all together, the theme wasn‘t. A few of the sweaters were definitely girl‘s sweaters — mother would cut out the tags so as to hide this fact from me. Fortunately, I wouldn‘t have to wear the things she bought me to school — I had enough normal schoolboy clothes. But I did wear them around the house at mothers request.


Chapter Eight — Surprises In The Guestroom

Mother and stepfather went out for the evening to the city, leaving early in the afternoon and would not return until late. I had at least eight precious hours to myself. I planned to dress up in the midnight blue gown with the black velvet bodice and rustling tulle lace petticoat. First, however, I‘d shower and wash my hair, then apply liberal doses of the scented lotions that mother had bought for me. Then I‘d slip into the pajamas and robe that Auntie had given me. After I showered, I went to the guestroom closet to retrieve the pajamas and robe and much to my surprise, there was the midnight blue gown, hanging on a scented hanger, the petticoat next to it. On the floor of the closet was a pair of mother‘s slightly worn black velvet Sabrina heeled pumps. But what was also hanging in the closet made my heart skip several beats — an exquisite light navy blue negligee, short robe, short chemise, tap panties, and pajama trousers, all trimmed with fine white flower petal Venise lace. They were made of luxurious silk surah— the label said they were ’Papillion by De Pledge‘. They that had to be new; they were not part of mother‘s collection. I stood silent for a full minute, collecting my thoughts, finally whispering "oh… my…" There in the closet, right across the hall from my room, in the beautifully decorated guestroom, was treasure. A minute later, the thought struck me that I had two pajama sets to wear, one given to me my Auntie, and another given to me by mother.

I next looked in the bureau drawers and my heart fluttered again. In the top drawer was a foundation set that matched the lingerie hanging in the closet — brassiere, garter belt, and pantie, and, disbelievingly, blue nylon stockings. There was also a side-zipper all-in-one girdle; unadorned white, the bands of elastic that defined the shape visible throughout the fabric, lifting the derriá¨re and flattening the tummy. It had four detachable garter clasps. The brassiere was slightly padded and had wide straps. This, too, was a new garment. Beneath this was a shape pantie, constructed the same as the all-in-one girdle; bands of elastic that lifted the derriá¨re and flattened the tummy, with four detachable garter clasps. There were also three new pair of silky panties, all high-cut briefs, adorned with lace; one each in pink, blue, and white.

In another drawer were several plastic garment bags containing many of my mother‘s sweaters and winter scarves, apparently put there for storage, including a favorite of mine — her oatmeal colored ribbed angora and lambswool sweater dress, V-neck, with mauve trim at the neck, cuffs, and hem, with a long matching mauve waist sash. I next looked in the vanity drawers and found that mother had emptied the contents of her unused cosmetic drawer in her vanity into the drawer. Another drawer contained a porcelain canister filled with dusting powder, a powder puff, and one of those gift boxes of makeup that stores sometimes sold as promotional items — buy some expensive cosmetics and you could buy the gift box at a much reduced price, or receive it free. It contained blush, eyeshadow, and lip gloss. Another drawer contained a combing set — silver-backed hand mirror, hair brush, and comb, all on a mirrored silver tray. I took out the tray and put it on top of the vanity next to the porcelain figurine.

I didn‘t know why mother had put these things in the guestroom. Deep down, I felt that she had put them there for me, but there was no definitive proof. There could have been other explanations, but the one that kept coming back was that she knew I was dressing in her things, that she considered the evening gown mine, and she left it there along with everything I‘d need for a complete ensemble, sans jewelry and other accessories. But it didn‘t matter at the moment, for I had a long luscious dressing to attend to.

I went to her room for her lapis and gold jewelry, sachets to pad the brassiere, and a blue satin hair bow, then to my room to fetch my radio/CD player, turning the radio to the local classical music station, and then downstairs to pour a glass of wine in our finest crystal stemware. Returning to the guestroom, I laid out on the bed the negligee, short robe, short chemise, tap panties, the foundation set, and the stockings and drew the drapes. I turned on the table lamps which resulted in the most romantic mood. I donned my white silk charmeuse pajamas and robe then sat down at the vanity to make up and brush my hair. Mascara brought out my eyelashes and I then applied cream foundation and powder. I used dark tones for my eyeshadow and cheek blush, and deep red lipstick.

In the guest bathroom where the venting was good, I smoked some hashish to heighten my senses. Returning to the bed chamber, I slowly removed my silk pajamas and donned the Papillion brassiere (and the sachets for padding), garter belt, and pantie (protecting my daintie with a linen hand towel). I sat back down at the vanity, sipped some wine, and began drawing on the stockings while the radio played ’Bolero‘. As I slowly drew the stockings up my legs, I remembered back to Auntie and Suzanne, the Susan Lane gown, and how Auntie remarked how I obviously knew how to put on stockings. I thought about the note she and Suzanne had left with the negligee (I had since destroyed it). I focused on the porcelain figurine of the lady drawing on her stockings — it was me at that very moment. "Oh, they know!" I whispered.

I started to ’titch‘ as I called it — making a quiet little clucking, or ’titching‘ sound with my tongue against the roof of my mouth, one leg or the other moving imperceptibly, rhythmically, erotically, rising up on my toes then back. My softly lit reflection in the antique silver mirror of the dressing table caused me to pause for several minutes, titching, fondling my long hair, thoughts of shame crossed with thoughts of pleasure. The dressing continued with the chemise, tap panties, negligee, and short robe. Another delicious hour or so had passed until I found myself standing in front of the oval dressing mirror, the lapis jewelry, the blue hair bow, the black velvet Sabrina heeled pumps, negligee and robe, completely overwhelmed. I hadn‘t even made it to the evening gown, for the negligee and robe, with the lapis and gold jewelry, were just so very, very stunning.

My boudoir, I thought. This was my boudoir that mother had decorated for me and left behind a lovely dressing and cosmetics. It was my boudoir, right across the hall from my room… I was such a sissy… A sissy librarian… Oh, how very shameful… In the quiet stillness of the house, soft classical music playing, sipping wine from fine crystal, dressed in fine lingerie, high heels, expensive jewelry, I stood at the mirror, knowing that the slightest touch to my daintie would induce a heavenly creaming. Saying my O‘s out loud, I managed to lift the negligee to reveal the dance panties, knowing that it would be impossible to remove them without creaming. I just hoped that the linen hand towel I had folded around my daintie would absorb what was sure to be a deluge of cream. I just stood transfixed, knowing there was nothing I could do but hope and give one more titch accompanied by a slight movement of my leg. Holding the negligee up, I let out a long moan of "Oh Evelyn, welcome to your boudoir", titched, and focused on my beautiful blue with white lace panties as I just burst open, each contraction accompanied by a loud cry. Thankfully, the linen hand towel protected the panties, and I was able to undress without wetting or sullying anything.

I was barely able to clean up and remove all evidence of my foray into the guestroom before my mother and stepfather returned home. I lay awake that night thinking about the treasures in the guestroom and wondering why mother put all those things in there. I also wondered if I had forgotten to put something away correctly and if mother would check.


A day or two later, mother bought me a really nice terry bathrobe set. The bathrobe was full length, white, and made of plush and soft puckered terry. It came with a long narrow towel that I surmised would be worn like a scarf beneath the bathrobe, and a tapered towel to be used as a turban for wrapping wet hair. She also bought a new towel set made of the same plush terry. A few days later, I was in the guest bathroom and discovered a matching wrap. It had two shoulder straps and closed at the top and waist with two white satin ties.


Chapter Nine — Packages And Sojourns

A few days later, I came home from working at the library to discover mother had received a package from Auntie. On the living room couch was the opened box and next to it were several garments. Mother was just starting to gather them up to take them upstairs. "Look what your Aunt Beverley sent" she said gaily. I tried to feign indifference, but mother ignored it, and proceeded to show me what Auntie had sent.

The first thing she showed me was the powder blue dress that Auntie and Suzanne had dressed me in and then taken me out. "Isn‘t this lovely?" she asked me.

"Uh… yea" I stammered. My jaw was slack and I was tingling all over.

Then a pair of charcoal gray woven wool and silk blend slacks, side-buttoned, the full legs a long liquid spill of beautifully draped fabric, and a knee-length fit-and-flare pleated skirt of the same fabric, also side-buttoned. These were matched with a cashmere/mohair blend V-neck sweater in charcoal gray with an argyle pattern of heather gray, dove gray, and white. The three items were made by Armani. Mother made some comments about the fabric.

"This is such a nice sweater. It would look really good on you" she said matter-of-factly.

"No thanks, mother" I stammered. I couldn‘t tell her that I agreed with her.

"Why not?" she retorted; "Just because it‘s a girl‘s sweater?" she asked, holding it up to me for size. "It would fit you perfectly, dear, and the colors are so nice for your complexion" she added. She didn‘t press me anymore about it and laid the sweater on the couch.

My eyes must have lit up when she briefly showed me a white crepe de chine chemise with a profuse point de gaze lace chevron at the bodice, flecks of pink and blue in the lace, with a white satin ribbon tied in a bow in the center, a matching dance pantie, the lace forming inverted pleats, and a matching long robe, bell sleeves, the shoulders adorned with the same lace. "These are from Jane Woolrich, a famous designer" said mother, "They are so very fine and nice". She then took everything upstairs.

Later, she called Auntie, and I overheard her saying "Oh, they‘re lovely. Thank you so much, Beverley. I love the Armani."

That evening, I had a chance to sneak into the guestroom for a brief moment and to my utter delight, everything Auntie had sent was hanging in the closet.


I didn‘t have long to wait to try them on, for that weekend, while my stepfather was away on business, mother and Mimi went to New York City to see a Broadway play. They left Friday evening and would return late afternoon Sunday.

Oh, how I loved being dressed in the powder blue dinner and dancing dress again! Oh how the skirt shimmered in the soft romantic light of my boudoir! I stood at the dressing mirror, classical music playing softly, swaying back and forth to allow the skirt to catch the light, a crystal wine goblet in one hand, my lipstick on its rim. I had traipsed through the house on my heels, pausing at every mirror to admire my ensemble, and now it was time. I stood at the mirror and began titching. Like before with the blue with white lace dressing, there was absolutely nothing I could do but let it happen. The movement of my leg was all that was needed to bring me to the edge and as the moment drew close, I breathlessly whispered "Oh, Evelyn, you‘re such a lady" as I creamed into the fine linen hand towel that was protecting my panties.

The Jane Woolrich chemise, dance pantie, and robe were so wonderful, so unbelievably sensuous — I was such a lucky lady to have such fine things! The Armani slacks, skirt, and sweater were delightful — such luxurious fabric — and the slacks and sweater were almost menswear-styled enough to give me the thought that I could wear them as a boy — ’oh my‘ I whispered while wearing them. Mother was right — the sweater did look good with my complexion. I couldn‘t decide what looked better with the skirt and sweater — black, white, or gray stockings. I needed more time to spend with these things.

I had tried to put everything back in its proper place before mother and Mimi returned, but I couldn‘t remember where everything went. If mother was checking the guestroom for signs that I was in there, there would be a strong possibility she‘d notice something.


A few days after their return, another package from Auntie arrived — this one containing a St. John two-piece knit; peach and gray tweed skirt, knee length and slim, and a waist length jacket, both lined with pink satin, and two tops — a matching pink silk and cashmere V-neck tank top and an ivory colored silk top. Auntie and Suzanne included a chiffon scarf with hues of peach, ivory, and gray that went perfectly with the suit. Then a pair of fawn colored rayon slacks and a fine silk and cashmere jewel neck sweater in a matching fawn with off-white trim at the neck, waist, and cuffs. The slacks were tapered with a fly front, a crisp pleat on the legs, and three pleats at the waist. Finally, delightfully, my eyes beheld a shimmering silver gray jacquard camisole, tap pantie, and pettislip, all trimmed with ecru bobbin lace. The labels said ’Natori‘.

Mother showed me the things, and when she got to the slacks and sweater, she said nonchalantly: "These are nice, aren‘t they dear? You know, they‘d fit you just fine. You could wear them to work — I think you should be dressing nicely for work — Melanie would appreciate it, I think; she thinks librarians should always dress nicely. You could wear this outfit to work and the one Beverly sent with the last package."

I huffed and made some stinging comment. Mother said "Oh, don‘t be such a sourpuss! Really, sometimes you‘re just impossible!"


Then, happily for me, mother went to New York for another weekend with Mimi — one last time before school started. The thought entered my mind that this might be the last chance I‘d have to play dress-up for a while.

I had been thinking about the problems I was having creaming into panties and perhaps sullying them. The linen hand towels weren‘t absorbent enough and they felt a little rough against my daintie, but until the linen became soaked, they were an effective barrier. A terry washcloth was better, but I didn‘t like the bulge in my panties. The day before my parents left, I was downstairs in the laundry room when I happened to look in the waste can and I saw an old pink cashmere twinset of my mother‘s. I retrieved it and saw that it had some holes. When my parents left for the city, I brought out my mother‘s sewing machine. (Mother had taught me the basics of using the sewing machine for sewing patches on my jeans. She thought it was a useful skill to know, and I agreed.) I cut a fourteen by three inch rectangle of cashmere, and a similar sized piece of a linen hand towel. I then sewed the cashmere onto the back of the linen, then folded the rectangle so that it made a sort of tube of five or so inches, and sewed this together. The result was a cashmere-lined cylinder about five inches into which I could insert my daintie (my daintie was rather small — I had measured it sometime ago — just for curiosity — and it was four or five inches, which was below average — yet another sign of my femininity I guess.) I sewed two ribbons on the extra flap of material; this flap would wrap around my sack and the ribbons could be tied together to secure the entire garment to my daintie. It was crude — sewing cashmere was a fool‘s task — but later that evening, it proved to be effective in preventing me from sullying my panties.

And so I had two delicious days. I cherished the St. John suit, especially with pearl and gold jewelry and the sheer cream colored silk top, the gray Natori camisole with ecru lace showing beneath the sheer silk, white stockings, and pink patent leather Sabrina heel pumps from my mother‘s closet. For foundations, I wore a gray set of my mother‘s. I experimented with the scarf, and finally decided on using it as belt around the skirt waist. The ensemble oozed old-money sophistication and contemporary elegance, something a well-heeled lady would wear for lunch and a bit of shopping. I was slowly disrobing myself of the ensemble in front of the mirror, titching, first the jacket, then the blouse, revealing the shimmering gray Natori camisole. As I slowly removed the skirt past my oh-so-stimulated daintie, an orgasm came on so quickly and powerfully that all I could do was to shout "oh… oh NO" as my cream gushed into the garment I had sewn — my ’‘daintie glove‘ as I was now calling it. If there was ever a test of its effectiveness, this was it — and it worked — but just barely.

I loved the rayon slacks and the cashmere and silk sweater — there was something about wearing menswear-tailored ladies slacks and sweaters that made me feel oh-so-daring. The sweater was roomy and I convinced myself that I could wear it as boy as my mother had suggested. Perhaps I should wear it to the library, I thought.


I took another hour or so and sewed another daintie glove, adding a few refinements here and there. Now I had two, so that I could wash and dry one while wearing the other. I also cut some remnants of the sweater into pantie napkins, sewing the edges to keep them from unraveling.

When Sunday afternoon rolled around, I was carefully putting everything back in its place, hoping to erase any evidence that I had been in the guestroom dressing up. To my horror, I discovered a run in the blue nylon stockings. Oh no! Here was proof positive! I made up a bunch of excuses in my mind in case mother asked me about it. But she never did.


Chapter Ten — Movie Nights In Silk

School started, and somewhat to my relief, my urges to crossdress lessened, probably because I was busy with school or maybe — hopefully — I was outgrowing my illicit desires. My schedule was different than any of my classmates in the neighborhood and carpooling wasn‘t an option, so mother had to drive me to and from everyday. My course load was incredibly easy; only two real classes — a government class and an English literature class, taught by my favorite teacher and academic advisor, Ms. Hunter. Ms. Hunter was very pretty and the subject of many teenage boys crushes. She was my height had a very nice figure, with shoulder length mousey brown hair that she would wear in variety of ways. I could have taken more advanced placement classes, but since I had already been accepted to Berkeley (providing I took the two classes), mother suggested that I just take it easy for once. I readily agreed.

My schedule was ideal, I had Friday‘s off and for the rest of the week I would arrive a few minutes before ten o‘clock and leave a few minutes before noon. I still played in the orchestra, which met on Wednesday afternoon.


While my urges abated somewhat, mother continued dropping little hints and suggestions. I had told my stepfather that I‘d cut my hair for school, but mother talked us out of it, saying that long hair was back in style. Just after school started, she took me to her hair stylist, Pamela. Pamela trimmed a few inches off, declaring that I had beautiful hair and making a couple of comments (that I was used to) about how she knew girls who‘d love to have my hair. She cut it so that it was mostly all one length, so that I could tuck my bangs behind my ears. An elastic hair tie would hold it all back nice and neat, and she showed me how to tie a simple rope braid. While Pamela was cutting my hair, mother bought some plastic hair clips, a faux tortoise-shell semi-circular hair clip, and an interesting device for putting up hair; a six inch length of foam over bendable metal. Pamela called it a ’bun curler‘ and demonstrated it on me so that mother could see how it worked. Starting at the bottom of my hair, she rolled my hair in the foam, bent it into a U-shape, and then fixed the bun with bobby pins. It made a very neat and elegant bun. (I thought about how I could use when dressing as proper young librarian.) Later at home, I was brushing out my hair and noticed just how femininely styled it was. I was turning into a girl, I thought to myself. The foam bun curler ended up in the drawer of the guestroom vanity. Mother said she bought the tortoise-shell hair clip for me and put it in my bathroom in the drawer with the rest of my hair grooming things.


Now that school was starting, I was pretty much resigned to not having any more weekend sojourns, figuring that mother wouldn‘t want to leave while I was in school. But then she told me that she and my stepfather were going to Europe beginning in the middle of October and would be gone almost the entire month of November, returning in time for Thanksgiving. My stepfather had some important business to attend to and mother was going with him to look for furnishings for the new house. While I didn‘t think she was particularly excited about moving, she was definitely excited about decorating the new house. She loved decorating, as did I, and she was going to immerse herself in turning her new house into a showplace — my stepfather certainly had the money to do so. While they were gone, Mimi would take care of me, driving me to and from school, fixing me meals, and keeping the house in order.

The thought of having a month to myself, except for visits by Mimi, dressing-up whenever the muse struck, turned my mood completely around. The anticipation put me on edge as I began to scheme and plan, and my desire to dress-up became almost irresistible. After the holiday was announced, whenever I had a little time to myself, I experimented with my hair, using a curling iron and trying out the bun-curler, thinking about how I would coif my hair for the dressings I was planning. I started using all the lotions and soaps that mother had purchased for me and noticed that they were having an effect — my skin as becoming even clearer and softer. And I would visit my boudoir in the evening, never dressing up, but going through the wardrobe, holding things up to me in front of the mirrors, mixing and matching things.

I began to save my allowance and other spending money that my mother liberally gave me and bought quite a bit of potent hashish for the holiday I was anticipating — the hashish so heightened my senses for dressing-up. It was not something I indulged in otherwise. I also prepared for the holiday by doing every bit of schoolwork I could do in advance, getting straight A‘s, doing extra work, all just to give myself all the free time I could. I didn‘t tell any of my friends that I‘d have the house to myself, lest they intrude on me.


Fall was approaching and the evenings and mornings became cool. Mother bought me a nice cotton pajama set in dove gray with peach trim; nightshirt, shorts, pajama bottoms, and long robe. Like everything she was buying for me lately, they were ladies-wear, but on the feminine side of androgynous. The pajama bottoms were cut wide and billowy. The material was very soft combed cotton, the nightshirt was long and the shorts were roomy and tailored like culottes. Later, I found a matching camisole and bikini pantie in the guestroom bureau. The camisole had wide adjustable straps in peach satin.


Thursday nights became our movie night. I didn‘t have classes on Friday, so there was no need for me to study — I could just lounge about. My stepfather was usually absent on Thursday evenings, opting to stay in the city and come home early on Friday afternoon. Mother would rent a movie or two, always a drama or romance and almost always featuring lavish production and costuming. They were typically older movies as she could trust them not to have sexually explicit scenes, something neither of us wanted to deal with together. Mother would make a bit of an event out of it, letting me have a glass of wine in exchange for wearing the silk charmeuse pajamas. She would wear one of her modest nightdressings and groom herself nicely. We‘d share a bowl of popcorn between us and watch the movie. After the first couple of movie nights, I started getting a little more comfortable wearing the pajamas and robe around her. In anticipation, I would bathe in the afternoon, washing my hair and using the scented soaps and lotions that mother had bought me. For the afternoon, mother would ask me to dress in the soft androgynous things she had been buying me, suggesting things like "Why don‘t you wear that new sweater I bought you? You won‘t wear it to school, so I‘d like it if you‘d wear it for me." Before coming downstairs in my soft sweater and slacks, I‘d sneak into the guestroom and don a pair of the panties from the bureau. After dinner, I‘d change into silk charmeuse set and mother would don one of her nightdressings.


One Tuesday, mother was going to be gone for the afternoon, returning in time for dinner. Mimi would drive me to and from the library. After school, mother picked me up and dropped me off at home, then left. I had an hour or so to kill before going to work. On a lark, I snuck into the guestroom and donned the blue Papillion foundations — pantie, garter belt, brassiere, and the blue stockings with the run in them. Over these I wore the short chemise and tap panties. I dressed in a pair of soft denim slacks, a heather gray V-neck cable-knit cashmere and lambswool sweater that mother had bought me recently, and then a blue and white patterned flannel shirt of mine; the flannel was soft and the shirt was a bit oversized. I left the shirt unbuttoned and wore it like a jacket. The shirt and sweater hid the brassiere well — there were no telltale bumps. In my school backpack, I put some lip gloss, a hair brush, the bun curler, and some bobby pins. Dark blue socks and loafers completed my daring dressing. Since Mimi was driving me to and from the library, and mother wasn‘t due home until an hour or more after I got back from work, I would be able to put everything away without her knowing.

At the library, I greeted Melanie and we chatted for a few minutes. I blushed when she complimented my sweater, and regretted wearing the shirt unbuttoned. I went upstairs and quickly shelved some books, then went to the upstairs bathroom and spent a few minutes putting up my hair into a fetching bun, leaving lots of little strands of hair to cascade down and about my face. I applied the lip gloss and left the bathroom. Feeling oh-so-daring, I wandered around the upper floors, doing a bit more shelving and a little homework. I was so much the sissy librarian, my hair done up, wearing a soft sweater, my lips glossed. It was all so thrilling; I had the floors to myself; no one disturbed me. I wished I had brought more things, like earrings, sachets to pad my brassiere, more makeup, maybe even a skirt and heels in my backpack. But the time to leave soon came and I went back to the bathroom and cleaned myself up, no traces of lip gloss, my hair back in a rope braid. I went downstairs to wait for Mimi. I almost had a nervous breakdown when mother showed up instead. The person she was going to meet didn‘t show, and she came home early.

"You look nice, dear" she said as I got in the car.

"Oh. It‘s just a little chilly in the library so I wore this to stay warm" was my excuse.

"Of course, dear" she said reassuringly. "You know how I‘d like you to dress better for work."

As soon as we got home, I went upstairs and quickly undressed and managed to get everything back into the guestroom unnoticed with one exception; the run in the stockings was now longer.

That evening, alone in my room, recalling the naughty fun I had at the library as a softly sweater‘d sissy librarian, my hair done up in a Gibson-girl bun, I had a most delicious creaming, dreaming of my upcoming holiday.


As they days rolled by and my anticipation grew, mother added a few more things to the guestroom. The first thing was a splendid antique three-divider dressing screen. The frame was dark wood, matching the rest of the furniture, with curved and round sculpted wood accents. One side was decorated with a faded tapestry depicting an idyllic garden party scene with ladies and girls in long regency dresses. This side faced outward. The other side was mirrored, the antique silvered glass, like the vanity mirror, had developed patina streaks. Mother had taken long lengths of pink and white tulle and draped them over the top of the dressing screen. My heart fluttered when I saw the screen for the first time, thinking of how enjoyable it would be to dress in its mirrors. Behind the dressing screen was a large circular ottoman upholstered in the same silver silk brocade as the loveseat and slipper chair. There were a few new silk brocade throw pillows on the ottoman. There was also a new porcelain figurine, this one of a girl in a flowing white dress holding a basket of flowers.


Auntie called one day and I spoke with her for quite a while. She knew all about mother‘s trip to Europe and said how she wished she could come out and take care of me but couldn‘t; she and Suzanne were in the middle of a remodeling project and had a couple of short trips of their own planned. She was very apologetic, and said she wished mother had told her sooner. She had me review mother‘s itinerary in detail for her, as well as my own weekly schedule. She asked about college and if I had been accepted at Berkeley and I told her I had.

"Have you accepted?" she asked.

"Not yet Auntie — mother wants me to wait until after she returns from her trip. She says I might change my mind, but I doubt it."

"Oh, I do hope you accept, dear. Both Suzanne and I are planning on it. It‘ll be so much fun to have you staying with us through the summer."

Suzanne had picked up the phone and interjected "Oh yes, you simply must come out here."

"I want to" I replied "but I promised mother."

"We understand" said Auntie. "I don‘t want to force you into anything."

Then Suzanne asked if I had seen that she had sent the blue dress.

"Yea" I replied, trying to sound indifferent.

"Well, I thought it should belong with you since it fits you so well" she said, a bit of tease in her voice.

"Right" I replied sarcastically. There was a pause and I suddenly felt bad for being sarcastic. Besides, I didn‘t want them to stop sending things to mother, so I said "I‘m sorry… Mother really likes the things you‘ve been sending. They‘re really nice."

"They are, aren‘t they?" said Auntie. "We‘ll be sending more soon, won‘t we Suzanne?"

"Oh yes" Suzanne said.

We said our goodbyes.


Mother and I were downtown one day and we passed by the town‘s best jewelry store. Mother paused in front to admire some of the jewelry. I noticed a little sign in the window advertising free ear piercing. Mother must have noticed me looking at the sign and said "I‘ve got an idea, dear — have you ever considered having your ears pierced? Everyone is doing it now. It would be a fun thing to do." I mumbled something, shrugged my shoulders, and said "Sure, why not?" Secretly, of course, I was delighted — no more using the band-aid trick that Auntie had showed me. The shop had very beautiful and expensive jewelry and we browsed while we waited for the salesgirl that would do my piercing to become available. I didn‘t feel uncomfortable admiring the fine jewelry, so I browsed the cases with mother. Mother and I both took a liking to a fine set of pearls and an antique silver filigreed hairclip. After a few minutes, I got my ears pierced (it didn‘t hurt as much as I thought it would). I got a pair of simple gold studs. Mother insisted that I also get a pair of small gold hoops as well. From that point on, Mother would often suggest — especially on movie nights — that I change my earrings to the gold hoops, saying it was good practice, for sanitary reasons, to change earrings occasionally.


Mimi started joining us on movie night. The first time, she brought a subtitled French movie she wanted to watch, and mother suggested she spend the night. She came over in the afternoon after I had bathed and donned my usual soft sweater and jeans with panties beneath.

I expected that I wouldn‘t be changing into the pajamas, but after dinner, mother told me that Mimi knew we‘d both be in our ’night dressings‘ and that Mimi would be wearing her own nightgown and robe. "We‘ll have our own little pajama party" said mother gaily. I had seen Mimi in a nightgown and robe whenever she spent the night; typically a long cotton nightgown and long robe.

Before I headed upstairs to change, Mimi appeared from the study wearing a new black cotton and wool blend nightgown, cut like a ballet dress. It was long and fluid with a shaped bodice, dropped waist and a full flare skirt, square neckline and cap sleeves. She looked elegant and graceful in it, and it flattered her figure. She was carrying a wool jersey robe in a blue check pattern which she put on after showing me her nightgown. "I‘ll make the popcorn while you two go and change" she said merrily, adding "…and a pot of your special tea, Dahl."

When I opened the guestroom closet to retrieve my pajamas and robe, I was face-to-face with the Jane Woolrich set; the white crepe de chine chemise and dance pantie on one padded satin hanger, and the robe on another. Mother had turned the hooks on the hangers so that the garments faced the closet door rather than the closet walls. My pajamas and robe hung between the chemise and robe, also on their own padded satin hangers.

Had mother done this as a tacit clue that she wanted me, or was allowing me, to wear the exquisite garments? I felt numb — I had been found out, exposed. Or had I? I was almost trembling, standing at the closet and staring at the beautiful chemise and panties that I so desired. I fingered the hem of the chemise and whispered ’oh my‘.

I began to undress out of my jeans and soft sweater. When I undressed down to my silky white panties, something came over me and I reached a decision. I shouldn‘t have done it, but was so in the mood. I slipped into the chemise and dance panties and then into my silk charmeuse pajama bottoms and top, then wrapped the silk charmeuse robe around me. I checked that the lacy chemise wasn‘t peeping out from beneath the pajama top — I didn‘t want mother or Mimi to see that I was wearing it. I was safe — the pajama top safely hid the chemise. After slipping into my bedroom slippers, I nervously checked myself in the mirror one last time and made my way downstairs.


Once I joined mother and Mimi downstairs I realized — too late — that Mimi had not yet seen me in the silk charmeuse set. But I needn‘t have worried — Mimi complimented me, saying "What a nice pajama set, Dahl. Your mother told me about them. You are so lucky to have such nice things to dress in, especially for lounging around in."

We sat down and started the movie. Mimi and mother curled up on opposite ends of the couch and I curled up in our big chair. I regretted wearing the chemise and dance pantie for it made me so self-conscious. But it was also so very thrilling, so naughty. But most of all, the thought that mother had displayed them for me to find… to wear… tumbled through my mind. About halfway through the movie, mother paused it and announced that she had to use the washroom. My heart almost stopped when she went upstairs instead of using the downstairs washroom — she might visit the guestroom and discover the chemise and dance panties missing. I followed her upstairs to use my bathroom and as a way to guard her from going into the guestroom. When I came out, I waited for mother at the top of the stairs. She came out from her room and suggested that we take the sheets off my bed for washing — it wasn‘t out of the ordinary suggestion for my sheets did indeed need washing. Together, we removed the sheets from my bed and I went downstairs with them, mother behind me. I was relieved that she had not gone into the guestroom. I put my sheets in the washer and started it, then came out of the laundry room. To my horror, mother was descending the final step of the staircase — she must have gone upstairs while I was in the laundry room. Had she gone into the guestroom to check? She didn‘t say anything or act out of the ordinary.

When the movie was over, I yawned, giving the clue that I wanted to retire to my room. Mother suggested that I spend the night in the guest room, reasoning that I was tired, I needed my sleep, and my sheets were still being washed.

"That‘s okay — I‘ll… I‘ll just put on the other set of sheets" I replied, not wanting to agree too quickly to her proposition.

"I know you could" she replied, "but it can just wait until morning. Besides, someone has to sleep there eventually, and I think it ought to be you, dear." Her tone of voice was gentle but with just a hint of knowing. "Mimi and I are going to stay up a while, but you should go ahead and go to bed."

"No… really… it‘s okay… but…" I trailed off, leaving a way out.

Mother took the hint and said "Oh, just go on and sleep in the guestroom. It‘ll be fine, dear… I want you to."

"Well… alright… if you insist" I replied flatly.

"I do. Goodnight dear. Give me and Mimi a kiss."

It was a bit of an unusual request to give them both a kiss, but I did so, receiving a peck on the cheek from both of them.


With the door closed and locked behind me, I let out a long sigh. I was thrilled to be allowed in the guestroom with its oh-so-feminine décor and its closet and bureau drawers full of treasures.

I turned the lights down low and was soon sitting at the dressing table putting my hair up, dressed in the chemise and dance panties and the matching long robe. I didn‘t want to go overboard with foundations or makeup in case mother or Mimi came to check on me.

I slipped into bed. The sheets were exquisite. The rest of the evening was exquisite as well, culminating in a toe-tingler, thinking about what my mother knew.


I came down to breakfast the next morning in jeans and a sweater after putting everything back exactly as I found it. Mimi had spent the night and we all ate breakfast together. Mother asked how I slept.

"Fine" I mumbled.

"How was the bed? Comfortable? The sheets are very nice, aren‘t they?"

"Uh-huh."

I changed the conversation as quickly as I could, asking them about their plans for the day. No further mention of my stay in the guestroom was made.


There were only two weeks left before my holiday. I dropped hints to my teachers that I might have difficulties getting to class during my parents holiday, but not mentioning that they‘d be gone. Neither of them seemed to care much — I was such a good student that my attendance really wasn‘t necessary — I could just ’mail it in‘ if I wanted. The teacher in my government class, Ms. Johnson, mused that she wondered why I bothered coming to class at all. Ms. Hunter said she understood, but that she enjoyed having me in class and would be disappointed not seeing me, but it would hardly affect my grade.


The next movie night rolled around. When mother picked me up from school, she said that Mimi was to join us for dinner and the movie, and would probably spend the night. She also said she bought me some new clothes and I could try them on when I got home. At home, she presented me a new periwinkle blue cashmere blend sweater, square neck, with roomy raglan sleeves and a wide elastic waistband. It was quite feminine, but I didn‘t say anything about it — I was getting used to her buying me such sweaters, and gave my standard non-committal thank you. She had also purchased for me a pair of slacks in a light gray and blue mottled wool and cotton blend. They had a high waist with a wide elastic waistband and big roomy legs. The waistband had a braided cord drawstring. She asked me to try them on, and I said I would after I took my shower.

As I was showering, I thought about how mother was slowly and step-by-step getting me to dress in ladies things. I didn‘t know what to think or do. I wondered just how far it would all go before my holiday.

Thinking about mother and what she was doing made me feel a little daring, and after drying my hair and putting it in a loose braid and applying lotions and powders, along with my gold hoop earrings, I snuck into the guestroom and donned the shimmering silver gray jacquard camisole and tap pantie along with the lacy high-cut pink briefs. I dressed in the new slacks and sweater — they were so soft and wonderful and made me feel the same. After putting on socks and a pair of loafers, I checked myself in the mirror and nervously made my way downstairs.

Mother was very pleased and asked me how I liked the ’new ensemble‘.

"They‘re nice, mother… thank you."

"I like it when you dress nicely around the house" she said, adding "you should wear nice things more often, like when you work at the library."

I didn‘t reply, but sat down on the couch.

"By the way; I bought you something else, too" mother continued. "Mimi and I were out the other day, and we both thought you needed a new set to wear for our movie nights — something warmer. We came across this set…" She disappeared for a minute into Mimi‘s room and came back with a large box from Nordstrom‘s.

"I thought you could wear these tonight" she said, handing me the box.

With a quizzical look on my face, I opened the box and removed an oh-so-soft three-quarter length silk and cashmere robe in slate blue.

"Isn‘t it wonderful?" she asked cheerfully.

"Uh, yes… yes it is. I like it a lot, mother" I replied honestly. The robe was androgynous enough that I felt I could reply truthfully.

"There‘s more" she said, nodding to the box. Beneath layers of pink tissue were a sand-washed silk smoky periwinkle blue pajama set; cap-sleeve nightshirt, pajama bottoms, and a matching tap pantie. They were unadorned of lace. The sand-washed silk felt exquisite on my hand. The labels said the color was ’moonglow blue‘. The robe and pajamas were a matched set, the blue of the robe perfectly complementing the blue of the pajamas. It was an beautiful set and must have cost a pretty penny.

I couldn‘t think of anything to say as I unwrapped the things and put them on the couch. My own mother had just given me a ladies‘ loungewear set! Part of me wasn‘t surprised, part of me was thrilled, but mostly I was numb.

"Aren‘t they nice?" she inquired, breaking my dumbfounded silence.

I took a deep breath and whined "Mother… these are for ladies."

"So? So are the pajamas from your aunt, and you like those, don‘t you?" she asked matter-of-factly.

"I… I know. I just wear them because Auntie gave them to me and you want me to. I… I can‘t…"

"Of course you can wear these, dear. It‘s not like I‘m asking you to wear a lacy nightgown or dress or something — they‘re just a pajama, shorts, and nightshirt. And a nice robe, too. Besides, ladies sizes seem to fit you better."

"Mother…" I whined again

"Now, now — don‘t be such a prude. Mimi and I so enjoyed picking these out for you; we‘ll be disappointed if you don‘t wear them tonight."

"Oh… alright… if you two insist…" I replied, rolling my eyes a bit while smiling. Of course I couldn‘t wait to try them on.

"Here -- I‘ll take them upstairs for you" she said, gathering them up. "Why don‘t you get the sheets off your bed for washing?" she suggested.

I followed her upstairs. She took the set into the guestroom while I took the sheets off my bed, nervous that she might open the closet and see that the camisole and tap panties were missing. I strained to listen for the closet door opening, but I didn‘t hear anything. When I joined her in the hallway, carrying the sheets, I saw that she had carefully laid the set across the guestroom bed.

"You can sleep in the guestroom tonight, dear. We‘ll worry about your sheets later."

"Uh… okay" I replied sheepishly.


When Mimi arrived, she told me how nice I looked. During dinner, she asked if mother had given me the new pajama set. "I hope you like it, Dahl" she said.

"Uh, yes — it‘s nice Mimi. I‘ll wear it tonight" I mumbled.

"We had fun picking it out for you; I‘m sure you‘ll look very nice in them" she added.


After clearing the table, mother gaily suggested we all go change into our ’bedtime things‘. Upstairs I went, entering the guestroom and almost swooning at sight of the treasures draped across the bed, put there by my own mother.

I took my time undressing and putting away the underthings I was wearing. I donned the bikini panties that matched the blue silk surah set, the blue high-cut briefs, and the blue silk surah tap pantie with its profuse Venise lace. I had to talk myself out of wearing the matching brassiere. The moonglow silk tap panties perfectly overlaid the panties I wore beneath. The pajama bottoms and nightshirt fit perfectly. Mother was right — ladies sizes did fit me better. I wrapped the wonderfully soft and warm robe around me, slid into my bedroom slippers, checked myself in the mirror and whispered ’oh my‘. I made my way downstairs.

Mother was wearing another of her modest peignoir and robe sets, this one in peach satin. The lapels of the robe were machine cut lace as was the bodice of the peignoir. (Of course, I had tried it on in the past. Although it looked nice, the fabric was run-of-the-mill.). Mimi was in the same black ballet gown and blue checked robe she had worn the previous movie night.

"Let‘s have a look" said mother, beaming. They were both sitting down and I was standing, feeling their gazes upon me. I untied the robe and opened it slightly. She asked me to take off the robe and I did so.

"They fit nicely, don‘t they? How do they feel? That fabric is so nice, I think."

"Yes… yes it is" I said, putting the robe back on.

Popcorn was made, along with my special tea, and the movie was started. It was an English period romance known for its lavish costuming — a definite ’chick flick‘. As before, Mimi and mother curled up on opposite ends of the couch and I curled up in the armchair. When the movie was over, I yawned and made my way upstairs to the guestroom while mother and Mimi stayed downstairs for a while.

This time, I stayed up and played, donning the blue silk surah foundations, padding my brassiere, and applying a bit of makeup. Standing in front of the dressing screen mirrors, I modeled some of the things in the closet, holding them up, evaluating them, and relishing them. I didn‘t try them on in case mother or Mimi knocked on the door. Eventually, I slipped between the sheets and had a delicious time before falling into a warm deep sleep.

The next morning, I came downstairs still wearing the new pajama set and robe. Mimi had spent the night, and we all ate breakfast together. I lounged about in the set and mother said that I obviously liked the set since I was still wearing it. I had to admit that I did.


My stepfather came home early that afternoon and we had a nice weekend together — I think he felt he had to bond with me. We went to the movies and saw an action movie, and ate at a really good restaurant and talked about finance. He made clumsy attempts to connect with me, but failed. But I appreciated his efforts.


There was one more week left before my parents left, and I was on pins and needles.


To be continued…

The Awakening of Evelyn - Book 3

Author: 

  • Evelyn D. Fairechild

Audience Rating: 

  • Adult Oriented (r21/a)

Publication: 

  • Novel Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

Other Keywords: 

  • lingerie
  • Petticoats
  • Soft Sweaters
  • Boudoir

Permission: 

  • Posted by author(s)

The Awakening of Evelyn

Book 3

Evelyn D. Fairechild


Evelyn is dressed by his mother and his holiday begins, supervised by Mimi.

Chapter Eleven — Mother Discovers She Has A Daughter

It was the last week before my mother and stepfather left on their month-long trip to Europe, leaving me alone to indulge in my shameful desires. My stepfather would be home on Monday and Tuesday, and leave Wednesday morning. Mother was going to meet him at the airport in Washington on Sunday morning. Mimi was going to drive her there on Saturday morning and spend the night with her -- mother asked me not to mention this to my stepfather, who assumed that they were driving down early Sunday. My school symphony orchestra was giving a concert on Friday evening, with me as the featured pianist.


Monday after school, I was downtown with mother. I went with her to pick up her furs from summer storage (one of the dry cleaners in town had a cold room for storing furs). She had a wonderful collection of furs, most of them given to her by my stepfather and some from her modeling work. Mother expressed her difficulties owning furs; she had realized the ethical issues involved, so she only wore them when she accompanied my stepfather to a party or function. She had a dozen or more things. My favorites were a white fox stole with a matching hand-warmer and pillbox style hat, a white fox capelet, a red fox bolero, a natural mink seven-eighths coat with sable trim, and a large natural mink throw. All the garments were stored in lightweight cotton garment bags.

Afterwards, I accompanied her downtown to a stationary shop. While she was inside, I left to stroll about, for a few doors down was my favorite ladies wear shop, "An Affair to Remember", a formal wear and bridal boutique. The shop was at the top of my ’pass by and admire the window display‘ list. Mother said she‘d come and find me in ten minutes or so. I sauntered past the shop, trying not to look conspicuous. There in its window was an indescribably feminine petal pink chiffon dress. The surplice bodice was pink tissue crepe silk with elbow-length chiffon flutter sleeves, the waist a wide corset of horizontal runched chiffon, and the skirt just over knee-length with a lettuce-hemmed crystal-pleated chiffon overlay over tissue crepe silk. I slowly walked past the window several times, pausing and admiring the dress, wishing it was mine, dreaming of how it would feel to be dressed so prettily. I must have lost track of time, for mother walked up behind me and gave me a fright.

"Did I scare you?" she laughed.

"Whew!" I answered.

"That‘s a lovely dress, isn‘t it?" she asked, acknowledging that she had seen me admiring it. I forget what I answered, but mother gave me a nice knowing smile

At home, I helped bring in the furs. She had me put them in the guestroom closet. She draped the mink throw over the loveseat.


Tuesday was my day to work at the library. When school was over, Mimi picked me up instead of mother. Mimi explained that mother had taken the train into the city to sign some paperwork with my stepfather and would be returning with him later that evening. She drove me home. While she was fixing lunch for me, I went to my room. I peered into the guest room; mother had laid out the charcoal gray woven silk slacks and the coordinated mohair blend argyle V-neck sweater. I opened the closet door to find the shimmering gray Natori camisole and tap pantie displayed, the hangers turned so that the garments faced the closet door. The matching skirt and pettislip hung next to them.

I had an hour or more before I was expected at the library (Melanie didn‘t care when I showed up). ’Why not?‘ I asked myself. A half an hour later or so, I came downstairs to have lunch with Mimi wearing the same outerwear I wore the last time I worked at the library: soft denim slacks, heather gray cable-knit cashmere and lambswool sweater, and my oversized blue and white patterned flannel shirt. Beneath were the blue foundations; pantie, garter belt, brassier, and the blue stockings with the run in them. (I really needed new stockings). Over these were the silver gray Natori chemise and tap pantie that mother had hung for me to find. In my backpack, safely wrapped in a plastic dry cleaner‘s bag to protect them from my dirty backpack were the slacks and sweater that mother had lain out. In another plastic bag were the black velvet Sabrina heeled pumps, sachets to pad my brassiere, the bun-curler, hairbrush, lipstick, and cheek blush.

Mimi dropped me off at the library and I made my way to the third floor bathroom, coming out many minutes later wearing the slacks and sweater and pumps, my hair done up, my lips painted and cheeks blushed. I didn‘t pad my brassiere on the off-chance I encountered someone — I would have enough to deal without reaching beneath my sweater to remove the sachets. Besides, there was something about being all dressed in ladies clothes, but not actually trying to pass as a lady, which gave me a special thrill. I had to walk carefully on my pumps — my heeled pumps clicked on the hardwood floor. There I was; the sissy librarian. I don‘t know how I managed to get anything done.

Mimi picked me up on schedule, and I was able to put everything away by the time mother and stepfather returned from the city. Somehow, I refrained from creaming that evening — my little escapade at the library had left me in such a mood.


On Wednesday morning, I said goodbye to my stepfather. We shook hands and he gave me an awkward hug. I had a full day of school as the orchestra had its final practice before the concert. Back home that evening, mother made the suggestion that I skip school the next day to hang out with her, saying that she might need my help to get ready for her trip. I readily agreed, saying I was all caught up on homework.

After dinner, she suggested that I slip into my new pajamas and that I spend the night in the guestroom. I agreed with little fuss, and soon came downstairs in the wonderful sand-washed silk pajamas and cashmere robe. Mother had changed into her mint green nightgown and robe. We watched a bit of television before bedtime. I was careful in the guestroom that evening as I wanted to save myself for my holiday.


When I came downstairs the next morning, still wearing my new set, I found mother nicely dressed in an empire waist wool jersey dress in dark blue with a floral pattern, a dress that I had briefly dressed in on a couple of occasions. I was always affected when I saw her dressed in something that I myself had dressed in. Invariably, I‘d feel subdued, being constantly reminded of my innermost feelings, my shameful desire to dress-up. My thoughts would be of how I had looked in it, the details about when I dressed in it — what accessories I wore, what underthings, and what emotions I had felt. Since the dress was one of her more classy daytime dresses, I assumed that plans had changed and she was going somewhere. When I asked if she was going somewhere, she replied she wasn‘t. I was confused, but tried not to show it.

"Dear? After breakfast, why you to take a nice shower and wash your hair; I‘ve got a little uh… surprise. Use some of that nice shampoo and conditioner I bought you, too, alright?"

What in the world was the surprise? I thought. The only conclusion I could come to was that she wanted to do something with my hair. Perhaps she was going to cut it. But I came to another conclusion, one that sent chills through me.

So upstairs I went and took a long shower, washing and conditioning my hair and lathering my skin with scented soaps and bath lotions. I dried off with a big velour towel and applied more skin lotion, then pulled on the soft combed cotton shorts from the pajama set mother had bought me, then into the plush terry robe and, finally, wrapped the terry hair towel around my long wet hair. I was about to change into jeans and a sweater when mother knocked on my bedroom door.

"Are you decent, sweetie?" she asked, opening the door slightly.

"Uh — yea" I replied.

She opened the door the rest of way and upon seeing me in my terry robe said "Perfect; don‘t change a thing. Now, can you meet me in the guestroom?"

My head was buzzing as I walked across the hallway to the guestroom. Mother was sitting on the bed, facing the door. Behind her, I saw that the peach and cream tweed St. John‘s suit and the pink silk and cashmere V-neck tank top were all hanging on the dressing screen. I could also see the exposed ends of hanger hooks facing out, which meant that something was hanging on the other side of the dressing screen.

"Come sit with me" she said, patting the bed next to her.

It was if I was in a trance as I walked to the bed and sat next to her. I knew that she was somehow going to confront me about my crossdressing — that was the only explanation. But beyond that, I had no idea. My skin felt clammy, my palms sweaty.

She turned to face me, tucking a leg beneath her. My legs were dangling over the side of the bed and she said "Go ahead and pull your legs up and sit comfortably, okay?" I tucked my legs beneath me.

She patted my hand.

"This is a little difficult for me dear" she began. "So just bear with me and let me talk."

She took a deep breath and gathered herself.

"Dear? I have a big favor to ask of you. I know you‘re going to think it very unusual, but I really want you to do it for me. I‘m asking you because I‘m going away for a month and when I return things are going to change around here — us moving to New York, you graduating then going off to school. And, to tell the truth, I‘m a little nervous about this trip… something could happen to me and I‘d regret not asking you to do this for me."

I was absolutely perplexed and more than a bit concerned for she was almost trembling. Why was she worried that something would happen to her and she‘d never see me again?

"Of course, mother, what is it?" I asked, preparing for a catharsis.

"Well dear, do you remember back when Mimi would buy outfits for her niece and you‘d try them on?"

My heart stopped beating for a moment it seemed then started up again, pounding in my chest.

"Uh huh" I croaked, my mouth dry.

"Well, I don‘t know if you knew, but I so enjoyed seeing you in a girl‘s dress. For just a few minutes, you became the daughter I never had…" She paused for a moment. I could tell she was gathering herself for whatever she was about to say. Finally: "What I‘m asking, dearest, is that today, would you please let me dress up as my daughter?"

I gasped. I tried to form some sort of response, but couldn‘t.

"Please, dear?" mother continued. "It would mean so much to me. I‘ve wanted to do this for such a long time and now I‘m afraid this will be the last chance. Please?" And then with a smile and another pat on my hand, she added "Pretty please?"

I somehow managed to whisper "Well… okay… sure, mother… if that‘s what you want…" My ears were ringing. How in the world was I going separate what mother was going to do to me from my own desires?

"Wonderful!" she exclaimed, clapping her hands together and then giving me a hug. "I have something all picked out for you to wear. It‘s hanging on the dressing screen behind us. But first, dear, I‘d like to set your hair. Come sit down at the vanity. I‘ve already heated some hair curlers." She took my hand and led me to the vanity. Once seated, she unwrapped the towel from around my head, quickly fetched a dry towel from the bathroom and vigorously rubbed and wiped my hair to dry it further.

"This will be so much fun, dear. I promise" she said as she began to comb my hair, humming to herself. She asked me about school and the upcoming concert as she worked some mousse into my hair and then rolled my hair into the curlers.

"Okay, dear… next we‘ll get you dressed while your hair is setting. There are some things behind the dressing screen. Go on now…" She placed her hand between my shoulder blades and gently guided me to the dressing screen. "There‘s a long-line girdle there, dear. Slip into it and zip it up."


In a trance, completely dazed and confused by what was happening I went behind the dressing screen to find the girdle lying on the ottoman. Next to it was the pair of white panties from the bureau and a new unopened package of nude nylon stockings. Hanging on the back side of the dressing screen were the shimmering silver gray jacquard with ecru bobbin lace trim camisole, tap pantie, and pettislip, I removed my robe and hung it on the corner of the screen.

"Can you get into the girdle okay?" she asked, standing on the other side of the dressing screen.

"I think so" I replied.

"You should put on the underwear too… you know… the panties… before putting on the girdle."

I slipped into the panties, wishing I had a pantie napkin. I struggled with the long-line girdle for a few moments, and then the sound of the zipper being zipped broke the silence.

"All set?" she asked. "Stockings next; I think you can figure it out. Just roll the stockings up before you put them on."

I almost said "I know" but caught myself. Finally, it was happening — no more silk pajamas, no androgynous dressings in soft sweaters and ladies slacks, no more furtive crossdressing — my mother was dressing me as her daughter.

"You‘ll need to clasp the stockings to the girdle. Just make sure your stockings are on nice and straight before you clasp them, okay? Just go slow. And after you put on the stockings, I want you to put on the other things hanging there as well; the half-slip, camisole, and pants."

"Do I need to?"

"Yes, dear, you do; they will help keep your dress from clinging. Now, while you‘re finishing up, I‘m going to fetch some things. I‘ll be back in a few minutes, okay sweetie? And dear? Thank you so very much for doing this for me."

My head was still buzzing as I opened the package of stockings. Why was she doing this? Was it doing it for me — because she knew I liked to crossdress? Or was she doing it for herself -- because she truly wanted to see me dressed as her daughter? Did she love me less because I was a boy and not the daughter she wanted? Didn‘t she know how wrong this was? Did she feel she could ask me to dress-up because she had discovered I was crossdressing already? Was she validating my desires? It was one of those rare moments when I thought about my natural mother — she certainly wouldn‘t have done this to me… or would she? Did it matter?

I began rolling a stocking up my leg, and felt the familiar chill of pleasure as the nylon caressed my skin. Other thoughts came to me. Was this some sort of trap? Was she going to confront me about my crossdressing? Was she going to ask about Auntie? After all, the dress came from Auntie… were they colluding together?

I could have yanked on the stockings and thrown on the daywear, but I didn‘t. I took time to relish the dressing. I decided I would keep mum about my desires, about how very much I wanted to be dressed as her daughter, to even live and be accepted as her daughter. I knew that it couldn‘t happen… or could it? I decided I‘d have to relax a little, to just let it happen and enjoy the moment.

"How‘s it going, dear?" she asked, returning just as I finished drawing on the pettislip.

"I guess I‘m done, mother."

"Well, come on out then. Let‘s see you."

I stepped out from behind the screen, forcing a bit of a smile, adjusting the strap of the camisole. "Is this okay?" I asked.

"Wonderful, dear; simply wonderful" she said, a smile on her face, her eyes twinkling.

I saw that she brought the pink patent leather Sabrina heel pumps from her closet, the very ones I had selected when I had worn the suit on one of my sojourns. She had also brought jewelry — pearls I surmised.


"Okay, next thing is to put on the top and skirt" she said, taking the hanger with the silk and cashmere top from the dressing screen, adding a remark about the fine fabric. She took it off the hanger and handed it to me, saying "You‘ll have to be a little careful pulling it over your curlers."

She helped me guide the top over my head, tugged at the hem to straighten it, and then fastened the single button in the back. She stepped back and gave me a look over. "Um… perhaps we should add a little padding. Now what could we use?" she mused. "I know —I‘ve got a couple of sachets in my room. Let me go fetch them."

She was back in half a minute with the pair of sachets that I always used to pad my brassiere. I wondered — did she know that I used them for that purpose? Or did she just think it up herself? I took the sachets from her, saying "Here, I‘ll do it" and stepped behind the dressing screen, coming out a minute later with the sachets in place.

"Much better!" she said gaily. "I‘m having fun, dear. Thank you so much for doing this. Are you doing alright? You don‘t mind, do you?"

"No — it‘s… it‘s okay, mother."


"Hey — just for old time‘s sake, would you mind calling me ’mommy‘ like you used to do when you were little? It would make me feel… I don‘t know… a bit more… comfortable, you know?"

"Really? You want me to call you mommy? That‘s just a little spooky."

She looked chagrined and said "Well… I guess it is… if you don‘t want to, that‘s okay."

"It‘s okay… mommy" I replied. "Why not?"

"And one other thing… Can I call you Evelyn? I know you don‘t like it, but it‘s such a nice name. And now that you look like my daughter…" She trailed off, looking more embarrassed than I was.

"That‘s fine, mommy. You can call me Evelyn." I had given up drawing the line — she was my mommy and I was her pretty daughter Evelyn — for now, anyway.


"Should I put on the skirt now, mommy?" I asked, breaking the tension.

"You‘re so sweet, Evelyn! Yes… the skirt‘s next."

She took down the skirt and unzipped it for me. I sat on the edge of the bed and drew it on. ’Relax‘ I told myself; ’just force yourself to relax and let it happen. You don‘t have to freak out… just let it be fun.‘

"You hold the skirt up and I‘ll zip it" she said.

I watched in the cheval mirror as my mother zipped up my skirt. It felt so… so natural, so accepted, I guess. There were, to my relief, no erotic feelings — just contentment.

"How does it feel, Evelyn? It seems a little loose" she observed.

"Yes, I think it is mommy." The girdle had smoothed my tummy enough that the skirt was a bit too loose.

"I know a perfect belt… hang on" she said, disappearing quickly down the hall to her room. A few moments later, she reappeared with a gold drop-chain belt. The gold chain was interspersed with big faux pearl beads. "Here, let me put it on — it‘s a bit confusing how these drop chain belts work." She wrapped it around my waist so that drop-chains fell down my left thigh, then pulled the waist chain tight and hooked it in the back.

I did a little turn in the mirror as mother beamed.

"That‘s better, don‘t you think?" she asked.

"Yes, I think so too, mommy."

"Now sit down at the vanity. I want to add a little makeup and try some jewelry." I sat down as she asked, unconsciously smoothing out the skirt.

"You did that just right, dear" she observed.


She opened a drawer, saying "I put some of my makeup in her, stuff I don‘t use anymore. Let‘s see… I think some pinkish lipstick…" She absentmindedly rummaged through the drawer, withdrawing tube of lipstick and putting it on the vanity top. She continued rummaging about, saying "…and some mascara… some eyeshadow… and, yes… some foundation cream… powder… and a bit of blush." She placed these things on the vanity top, along with a small triangular makeup sponge. (I had always wanted to use the sponge, but couldn‘t risk leaving it in the drawer all stained with makeup.)

She started with the mascara, telling me that you always started with mascara so that in case you missed and left a smudge, you could wipe it off cleanly. She handed me the mascara brush and gave me a bit of instruction.

"You‘re doing really well, dear" she said as she watched me. I had tried to make it look like I was unfamiliar with putting on mascara, but I guess I didn‘t. She began telling me about her modeling days when she had makeup artists do her makeup for her, how making up for the camera was different than normal makeup.

Next came some cream foundation. "You need just a little bit of this, Evelyn — your young skin is so flawless. But a little foundation cream helps with the blush." She applied a few streaks of the cream to one cheek, then smoothed it out with the sponge, telling me how one should always do one side of the face before doing the other; otherwise, the foundation cream would dry up on the one side while working with the other side. She applied it to the other cheek. Next she opened the compact of face powder and patted it on each check, then smoothed it out all over.

Eyeshadow came next. She told me how eyeshadow should go from a light shade starting at the nose to a darker shade on the outside. Then she did my cheek blush. Finally, she had me do the lipstick, telling me how the professionals applied lipstick using a brush, first outlining the lips with a pencil.

"You look really, really cute, dear" she said when we were finished. "Now I think that pearls would look really good with this outfit, don‘t you?"

"Yes mommy."

She had brought her single strand necklace of pearls from her room and now placed it around my neck, clasping it in the back.

"These are very nice pearls, aren‘t they mommy?" I asked.

"Yes… I love pearls" was her reply. "These are some of my best pearls. This set came from Japan years and years ago. They‘d be really expensive if you bought them today. Now I want you to put on these earrings, okay?" She laid the pair on the vanity top — four pearl drop earrings.

"Of course, mommy; I guess it‘s good that I got my ears pierced, huh?"

"Yes, I‘m so glad you did. There‘s not much selection for clip-on earrings."

When I had finished with the earrings, I shook my head a little and gave myself a look in the mirror, gently pulling aside a strand of hair that had escaped the curlers to get a better view of the earrings.

"Isn‘t this fun? You look so cute. I‘m so glad you‘re having a bit of fun with this dear. Let‘s put on the jacket and then I‘ll let down your hair."

As I stood at the cheval mirror, she stood behind me and helped me into the jacket, then came around in front to adjust the collar. She stood back to admire the dressing, saying "You look fabulous, dear. Just look at you."

She had me sit down again at the vanity. She clasped a two-strand pearl bracelet around my left wrist and had me add a peach Bakelite bangle bracelet. Then she began taking the curlers out of my hair. When they were all removed and my long curled hair cascaded down, she used the comb to arrange and fluff it out a bit.

"Oh, Evelyn, you‘ve got the prettiest hair. Just look at you. No one would ever guess you were anything but my daughter. You are just so so pretty. Now let‘s see if these heels will fit you."

She handed me the heels. I began to cross my leg to slip into it when she said "No — that will stretch the skirt fabric. Besides, it‘s so unladylike. Bend down instead." When I bent over, my hair cascaded down.

"Do they fit alright? They‘re probably too tight, huh?"

"No… they fit fine, mommy."

She helped me stand, taking my hand, cautioning me about wearing heels. She stood me in front of the cheval mirror. She was standing behind me and ran her hands slowly down my arms, saying "Just look at you, Evelyn. You make the prettiest girl. I could get you a modeling job just like that" she said, snapping her fingers. "What do you think? Do you mind dressing up as a girl?"

I had to pause and think of an appropriate response.

"No. I don‘t mind mommy. It‘s kind of fun." I considered responding with the whole truth, but couldn‘t bring myself to do so. Besides, she probably knew.

"Really? I‘m glad to hear you say that, dear. You know, maybe while I‘m away…" She didn‘t complete the sentence, leaving it hanging there to sink in.

After a few moments, moments that I think she was waiting for me to say something more, she said "Let‘s go downstairs. I‘d like to take a couple of pictures of you as a keepsake. Don‘t worry, I‘ll send them away to get developed — no one will see but you and me, okay?"

"Well — as long as no one ever sees them, mommy, I guess it‘s okay."

"Great. Be careful walking down the stairs on those heels."


We went into our formal parlor. She produced a disposable flash camera and had me sit on the couch and instructed me to sit with my knees together with my hands folded in my lap. She took a couple of shots. Then she had me stand by the grand piano, first with the jacket open, then with it buttoned. Because of her modeling experience, she knew how to pose me, having me bend lean against the piano, one knee slightly bent, my elbows bent, hands gently clasped. She also had me play the piano while she took a couple more shots.

It was nearing lunchtime and the roll of film was half-way done. "No use wasting film. Let‘s have a little lunch then try a few different accessories on you, like that scarf that Beverly sent with the suit."


Together, we made soup and a sandwich. "This is so much fun for me, Evelyn" she said as we sat down to eat. "Is it fun for you?"

"Umm… yes mommy. I‘m having a nice time" I replied.

"Oh wonderful — I‘m so glad to hear that."

She told me that Mimi was coming over for dinner and the movie and that she wanted it to be a special night since it was our last movie night together for a long while.

"Just so you know… you don‘t have to change before dinner if you don‘t want" she said after a pause, speaking barely above a whisper.

I let out a grunt and then whined "Mother…"

"Mimi wouldn‘t mind at all, dear… really…" she replied in a non-committal way.

"Well… I‘d rather not" I replied, hiding my angst.

"Well, alright then. But that doesn‘t mean you can‘t wear something nice. I‘m planning on wearing something nice and so is Mimi."

"Uh… okay, mommy."

"I‘ve got an idea on what you could wear. We‘ll discuss it later, okay?" She then changed the subject to Mimi, saying how she wanted Mimi to stay with me while she was gone. Knowing that I would object as I had been doing, she quickly added "Don‘t worry dear — I‘m sure you two will have a fine time together. She‘s really looking forward to it. Don‘t look so sad, okay? I think you‘ll really enjoy having her here."


We went upstairs to her room and together selected a couple of hairpieces, some costume jewelry in coral pink and ivory, a scarf clip, and beige chiffon scarf. As she was selecting things, she would ask my opinion. I could have responded with "Whatever you say, mommy" but instead got into it, agreeing that the jewelry would match the suit colors, that the colors and pattern on a particular scarf was too ’busy‘.

"You‘ve got such good tastes, Evelyn" was her response.

She sat me down at her vanity to fix the first hairpiece; a peach and cream layered crepe bow. Just as she finished, the doorbell rang.

"Oh, drat!" she exclaimed "who could that be? I‘ll go answer it dear… you just stay here."

"Uhhh… of course I will, mommy" I replied with a chuckle.

"You‘re so sweet" she said, kissing me on the cheek and going downstairs.

I heard her open the door and say loudly "Barbara! I completely forgot! I‘m so sorry. Come into the study. Do you want some coffee?" I heard the door close and some muffled conversation as they moved to the study. Then I heard mother say "I‘ll be right back — I‘ve got to go upstairs for a moment."

Back in her room, in a quiet voice, she told me that it was Barbara Higgins from the historical society. She had come over to have mother sign some checks. Mother had completely forgotten that they had agreed to meet that afternoon. "I‘ll try to get rid of her as quickly as possible Evelyn, but this may take a half-an-hour. Why don‘t you pass the time experimenting with different accessories and things and pick your favorite look? And maybe you could do your nails, too — you can choose the color." She gave me another kiss on the cheek and left.


She was gone for over an hour. I spent the first half-hour or so experimenting with combinations of carves and jewelry, finally deciding on the coral pink and ivory jewelry with the chiffon scarf Auntie had sent.

I found myself sitting at her vanity studying my reflection. So many different emotions were churning inside of me, so many questions. It had to be a dream… this really wasn‘t happening. Both my mother and her sister had now crossdressed me. Had they found out my desires and were just coddling me? Or was there something else, something I didn‘t know? My eyes moistened — I was on the verge of tears. I had to dab my eyes with tissue and blow my nose ever-so-quietly so that mother‘s guest didn‘t hear. I just didn‘t know what I was going to do with myself, with my future. I needed something to take my mind away from all these thoughts, so I painted my nails with blush pink polish.


I heard mother say her goodbyes and soon she was back in her bedroom with me. Her first comments were about my selections, telling me how nice they looked, that I had such good tastes.

"And you‘ve painted your nails, too!" she exclaimed with delight.

"Yea… I got kind of bored" I replied.

She must have noticed my moist eyes, for she asked with great concern: "Dear… have you been crying?"

"Oh — no; I had to sneeze and I didn‘t want to make any noise, you know" I lied.

"Are you sure?" she asked again. "I don‘t want you to cry, sweetheart. You‘re not crying because I‘ve dressed you as a girl, are you?"

"No, mommy — I haven‘t been crying" I replied unconvincingly.

She didn‘t believe me, for she continued "I‘m so sorry, dear. I shouldn‘t have done this to you. I‘ve been so selfish. I shouldn‘t have told you about my wishes for a daughter. You poor thing, you, you were just trying to keep your mother happy. I just thought… I don‘t know… I just thought you would like it since… you know… It doesn‘t matter. Do you want to undress now?"

"No mommy. It‘s fine. I don‘t mind" I replied, my head swirling with questions. "I haven‘t been crying — honest. Everything‘s fine…"

"Really? Are you sure dear?"

"Yes mommy, I‘m sure."

If ever there was a moment when she would confront me about my crossdressing, it was now. If ever there was a moment when I would admit to her how much I like crossdressing, it was now as well. But neither of us could take the initiative; it was all left unsaid.


Her mood turned cheerful. "Let‘s go downstairs and finish the roll."

She had me pose by the dinner table by the candelabra and chandelier. She had me put the candelabra on the grand piano and pose by it. The roll was finished with me sitting at the piano and playing. I continued to practice my piece for the concert as mother started to prepare dinner. As I played, my nerves settled down and my playing flowed. During a pause, mother came in and told me how beautiful my playing was.

"Oh my goodness — look at the time. Mimi will be over in less than an hour. I need to change. Are you sure you don‘t want to wear a dress for dinner?"

"I‘m sure, mother" I replied, sounding exasperated.


We went upstairs together and she followed me into the guestroom. She helped me out of the jacket and hung it on its hanger, putting it back on the dressing screen. The jewelry, scarf, hairpiece, and drop-chain belt came next, then the heels, skirt, and top, leaving me standing in the pettislip and camisole.

"You know…" she mumbled as she stood at the closet "…I think you should wear this for dinner." She held up the fawn colored rayon slacks and the coordinate silk and cashmere jewel neck sweater with off-white trim.

"Oh mommy…" I said with a bit of exasperation, trying to form an excuse. But she easily talked me into it, saying that the slacks and sweaters were perfectly acceptable and appropriate dinner wear and that she and Mimi would appreciate my attempt to "dress nicely tonight — we are."

She laid the slacks and sweater on the bed.

"Now, about the movie tonight — what pajamas and robe were you planning on wearing?"

I replied that I‘d probably wear the white silk set from Auntie.

"I‘d really like for you to wear these tonight" she said, removing the blue silk surah pajama bottoms and short chemise from the closet.

"Mommy… no…" I whined. But again, she somehow convinced me, telling me that it boys and men used to wear "things with lace all the time" and that I could wear my new cashmere robe which would hide the chemise, and that Mimi really wouldn‘t care. "Besides, if you wear it tonight, Mimi won‘t think it unusual if you wear these while I‘m gone" she said with a pleasant smile.

It was that last comment that worked. She laid them out on the bed next to the slacks and sweater. The tap panties were attached to the same hanger as the pajama bottoms, and when she laid the pajama bottoms on the bed, she laid them so that the tap panties were displayed on top.

"Now… there‘s some cold cream in the bathroom — you can use that to remove your makeup if you want — it‘s better than soap. And I‘m thinking that these slacks may be a bit tight around your waist. You might want to keep your girdle on."

"Okay mommy" I breathed.

"Thank you dear. Now I‘ve got to go get ready." She closed the door behind her.

Tingling all over, I dressed for dinner. I couldn‘t wear the all-in-one girdle because the cups would be seen beneath the sweater, so I changed into the shaping pantie, attaching my nylons to its garters. I also wore the silver gray jacquard camisole and tap pantie beneath the slacks and sweater. I removed my makeup with the cold cream as mother had suggested, leaving behind little traces that I smoothed out with a sponge. I tied back my hair with an elastic band, but it didn‘t help much — my hair still had its curl. I had a little moment of indecision about earrings, but I went ahead and put on my small gold hoops.

I had barely removed my nail polish when I heard Mimi arriving. I checked myself in the cheval mirror — I was much too feminine; the rayon slacks were a long spill of creamy liquid down my legs, my derriá¨re a bit too curvaceous, the sweater too soft and girlish, my long hair curling down my back, my gold hoop earrings flashing in the soft light beneath strands of hair, flecks of nail polish on my fingernails, and my face showing still showing the effects of the makeup I had worn earlier that day. I slipped my feet into a pair of my tan loafers and nervously came down the stairs.


Mother was wearing a fifties style cocktail dress; bouffant skirt with a front buttoned blouse, wide fabric belt, and a high stand-up color. The top was organza and the skirt made of multiple layers of ninon and organza. The color was a striking moss green, a color that mother wore so well. Beneath the rather sheer organza top she wore a dark green camisole. She had chosen jade and gold jewelry and a pair of high de Orsa stiletto heels.

Mimi was equally striking in a pair of silver blue chiffon palazzo slacks matched with a beautiful beaded blue bustier and a sweeping silver blue chiffon jacket embroidered with blue thread, and dark blue pumps. Her jewelry was minimal — just a pair of silver earrings and a couple of silver bracelets. Her hair was brushed out with mousse applied to give it a bouffant style, and she had done her makeup.

"Wow!" I exclaimed "look at you two!" complete forgetting about my own dressing.

"I told you we were dressing up tonight, dear" she said, taking a turn. "Doesn‘t Mimi look fabulous?" she asked, prodding me.

"Oh yes, Mimi. You look really nice" I quickly replied.

"And so do you, Dahl" she said, looking me up and down. "I see your mother finally got you to wear those slacks and sweater. They are very nice, no?"

I just blushed. Mother interjected, saying "I practically had to beg, but I finally got to him to try them on. You look very nice, dear" she said, giving me a look.


We soon sat down to eat. Mother had me light the candles on the candelabra. We had a nice easy conversation, talking about mother‘s upcoming trip, my upcoming concert — they wanted to hear my piece after dinner — and how my job at the library was going. Mother mentioned again how she thought I should wear nicer things to the library, like "those slacks and sweater you‘re wearing."

"You know, Mimi, I think Dale is looking forward to have you stay with him" she said during a lull. "I think you two will have so much fun together."

"Yes, I think so too, Ellen" replied Mimi, giving me a slight smile.


I played my piano piece after dinner while mother and Mimi lounged on the couch. The outline of the garter clasps on my pantie girdle showed when I sat down on the piano bench. I doubted mother or Mimi saw the outline. When I was finished, mother said "Well, it‘s time for us girls to slip into our nighties and watch our movie. It‘s a classic — ’Funny Face‘ staring Audrey Hepburn. It‘s the last movie night we‘ll have together for a while. I asked Dale if he wouldn‘t mind wearing those nice blue pajamas tonight, Mimi."

Mother‘s comment about ’us girls‘ left me blushing.

"And…?" asked Mimi.

"He said he would."

"Wonderful. Well, let‘s all go change then."

Mother and I headed upstairs while Mimi went to her room.


I was unconscious at this point. I finished undressing, putting the daywear back on hangers and hanging them from the dressing screen. I removed the stockings and squirmed out of the girdle, then the panties, leaving them all on the ottoman. I then dressed in the exquisite set, adding the matching bikini from the foundation set in the bureau drawer. I tied the long white silk charmeuse robe tightly around me.

Mimi was waiting for me — mother hadn‘t come downstairs yet. She had started a fire in the fireplace — the first of the season. I stopped and gasped when I saw her; she was wearing a black lace halter top one-piece pantsuit and black chiffon robe trimmed with black marabou. The one-piece pantsuit had enormous flowing legs and was backed with white satin. She was holding a glass of sherry.

She smiled when she saw my expression and, putting down the sherry glass, put her hands on her hips, opening the robe to reveal all of the one-piece. Smiling, she asked if I liked it, and I stammered something.

"I‘d like to see your things, Dahl" she said coyly.

"Um…"

"Oh, come on, Dahl. It‘s alright — I know… your mommy likes you to wear nice things, even if they are ladies things."

A moment later, mother came down the stairs, rescuing me. She was wearing her beautiful and diaphanous pink robe and nightgown. It made me very uncomfortable — I was expecting her to wear one of her more modest night dressings. Although the set wasn‘t revealing, it was very romantic. Not only that, but it made me think of the times I had dressed in it, and the spectacular creaming I once had while wearing it.

"Well, look at us" she said gaily, bouncing over to the couch, saying that she hadn‘t worn the set for "the longest time — I thought tonight would be a perfect time."

I quickly took her cue and moved to sit in the chair.

"Do you like your pajamas dear?" mother asked, adding "They must feel nice, huh?"

"Yes mother… yes they do."

"I‘d like to see them" added Mimi.

"So would I dear" mother replied.

"Well… only because you insist" I mumbled as I untied the sash of the robe, doing so quickly. I let my robe hang open, not parting it.

"They‘re so lovely, aren‘t they Mimi?" asked mother.

"Oh yes… very beautiful…"

I hurriedly wrapped the robe back around me and sat down. Mother handed me a glass of sherry.

I started the movie, wanting to avoid any more conversation or confrontation about my ’lovely things‘.

It was all so incestuous, so salacious; mother dressed in the lovely and romantic night dressing, Mimi in her black lace and chiffon, and me in the most feminine silk surah set, my ears adorned with gold hoop earrings, the fire in the fireplace and the sherry softening the mood, and the scenes of Audrey Hepburn‘s dressings unfolding in the movie. Mother had to have known the affect it would have on me.


When the movie was over, mother said "Well, we‘ve got a busy day tomorrow, dear. I‘ve got last minute errands and I have to pack, and then there‘s your concert. I think we should close down and go to bed. You can spend the night in the guestroom, alright?"

"Okay"

"Wonderful. Mimi and I are going to stay up a while — there‘s some things we need to talk about."


I went right to bed and lay there stunned. So many thoughts went through my mind. How could the day have unfolded without the finality of me admitting that I loved to crossdress? Or without mother confronting me about it? She made it all seem as if I was doing her a favor instead of the other way around, how she went out of her way to ask if I ’minded‘ being dressed. But also… what a wonderful way to start my holiday — my mother opening all sorts of doors for me to spend my time dressing up in the guestroom and even sleeping in the guestroom. The only real issue was Mimi and how I would have to hide it from her.

It took a while, but my fingers began to explore my silk panties I was wearing. I desperately needed to cream in order to clear my thoughts and sleep. But I also wanted to save myself, and I knew if I creamed, I would probably have feelings of remorse and shame. I thought about mother wearing the beautiful and alluring pink chiffon nightgown and robe and Mimi in her salacious black lace one-piece. How incestuous… how salacious… how utterly shameful… I compromised by taking a velour hand towel and squeezing hard on my stimulated daintie when the precipice approached so that my orgasm was short and shallow. It seemed to have worked — I obtained some relief, but I avoided feelings of remorse. I drifted off to sleep, avoiding any thoughts of my holiday by focusing on my piano piece.


Chapter Twelve — The Lovely Ms. Hunter

I came downstairs the next morning wearing my soft combed cotton pajamas — camisole, bikini, pajama bottoms, nightshirt, and robe. Mimi was in the kitchen, wearing an apron over her soft denim long skirt and black turtleneck sweater.

"Good morning, Dahl. How are you?" she asked cheerfully.

"Wonderful, Mimi; good morning to you" I replied.

Mother came downstairs shortly thereafter. She was cheerful and announced that she had a wonderful time the previous night and had slept well. "In fact" she continued, "everything about yesterday was wonderful."

I blushed, thinking about everything that had unfolded, and hoped that neither she nor Mimi would bring up my crossdressing. I needn‘t have worried for we were soon eating breakfast together and discussing the day‘s activities. Mother had a busy day ahead of her and would be leaving shortly. She said she was going to use the guestroom as a staging area for packing. I said I‘d be practicing my piece for the rest of the morning. We agreed that the best time for Mimi or mother to take me to school was around two o‘clock. I could do some homework at the library and then join the rest of the school orchestra for practice. We‘d meet up for dinner and then both Mimi and mother would come to the concert. They‘d arrive around intermission — I wasn‘t playing until the second half and they needed the time to get things done. Beside, the first half was the junior orchestra and choir — nothing missed there.

After making sure that I took my usual vitamins, mother left, leaving me with Mimi. I went to my room and changed out of the pajamas and into jeans and a sweater. I spent most of the morning practicing my piece, noticing the flecks of nail polish that I had missed. While I was practicing, Mimi brought me a pot of my special tea. Mother came home for lunch and I changed into the clothes I‘d wear for the concert. As usual, we were to wear all black while performing and I chose a black lambswool sweater mother had bought for me instead of my usual black shirt. But I also wore the pink silk panties from the guestroom bureau.

Just before we were to leave, I peeked in the guestroom and saw that mother was indeed using it as a staging area, a place to pack her things — a couple of suitcases were on the bed along with various clothes.


I tried to study in the library, but just couldn‘t concentrate, thinking about the events of the previous day and the morning, going to the bathroom to find myself in the lacy pink panties. I wrote down some thoughts about the upcoming holiday in florid and feminine script, writing down what ensembles I‘d wear. I tore these notes up and flushed them down the toilet. Finally, practice came around, and then mother and Mimi picked me up for dinner. We ate at our favorite Japanese sushi restaurant.

As we were waiting to be served, Mimi excused herself to the restroom. Mother cleared her throat and said "I‘ve had a wonderful day with you yesterday, dear" patting me on the knee. "Thank you so much for letting me play dress up with you… and for letting me call you Evelyn… and for calling me mommy. It meant a lot to me, sweetheart. Maybe when I get back, we could more days like this. That is, if you don‘t mind."

"No mommy, I don‘t mind" was the only way I could reply.

"You‘ve made me so happy dear. And I think that you and Mimi are going to have such a nice time together; she‘s really looking forward to it. She told me she thought it was so cute and sweet that you wore those pajamas last night and that you didn‘t make a fuss about it."

The conversation ended when Mimi arrived back to the table. We were all hungry and dove into our food. We were in a bit of a rush and they had soon dropped me off at school.


Mother and Mimi arrived just before intermission; before I was to perform. I met them briefly in the lobby. She asked if I would be able to get a ride home — she needed to do some last minute packing and wanted to leave after I played. Ms. Hunter, my English teacher, was standing nearby. She was dressed in a black cowl neck sweater and a long burgundy skirt. She wore a wide leather belt around the sweater and a long gold chain necklace. She was made-up for the evening and looked fabulous. I looked around for her date, but didn‘t see any suspects.

"Excuse me" said Ms. Hunter, addressing mother. "I couldn‘t help overhearing. I‘d be delighted to give your son a ride home" she said, extending her hand to mother. Mother knew her, of course, but Ms. Hunter said out of courtesy "I‘m his English teacher and academic advisor, Nancy Hunter. It won‘t be a problem at all. I think your house is on my way home." Mother thanked her and accepted her offer. She then explained how she had last minute packing to do because she was going on a long trip; I guess she felt she needed to let Ms. Hunter know that she didn‘t normally ’bail out‘ on me and that this was a special circumstance. I wished mother hadn‘t told her about her trip and how I‘d be by myself for almost a month; I was trying to keep it secret from everyone. On the other hand, I was thrilled that Ms. Hunter was giving me a ride. All the other boys in my class would be jealous if they found out that I got a ride home with Ms. Hunter. It was at that point that Melanie appeared, looking very nice herself in a long silver gray tapestry pattern skirt and a black surplice wrap blouse with a side tie. After greeting her, mother introduced her to Ms. Hunter. The conversation was brief for it was time to be seated and I had to go.

My solo went off really well. Somehow, I was able to overcome my nervous energy and find that sensuous and lyrical frame of mind that made my playing so expansive and expressive. The realization that I was performing in front of the school while wearing pink silk panties and a soft girlish cashmere sweater helped me reach that elusive state.

After the concert, Ms. Hunter was waiting for me outside. She addressed me by my first name. Since she was my academic advisor and had access to all my records, she knew my first name was Evelyn and that it was an acceptable boy‘s name in years past. She was the one who made sure that my name wasn‘t on roll calls, knowing how much I‘d be teased by classmates. On the drive home, she told me how much she enjoyed my playing and that the only reason she had come that evening was to hear me play. "Evelyn" she said "you play with such exquisite sensitivity. I can almost feel every note. Please let me know whenever you have a recital — I so want to come to hear your beautiful playing."

I was deeply flattered. Knowing that she — this beautiful woman — liked my playing so much gave me chills. She changed topic, asking a few mundane questions, including questions about mother‘s trip. Then she said "Evelyn is such a beautiful name. I know you can‘t use it around school; everyone would tease you about having a girl‘s name. But I have to ask — did your mother expect to have a girl and named you that anyway, or is it an old family name?"

"An old family name" I lied.

"Well, then, perhaps after you graduate, you can start using it."


Mother was waiting for me. She was dressed in her mint green peignoir and robe. She gave me a big hug and told me how wonderful I was. She poured me a glass of nice wine. It was late; mother said I looked tired. I admitted it was.

"Well, off to bed with you then. I‘m still using the guestroom for packing, so I‘ll try to be extra quiet. I‘ll see you in the morning, dear."

We both went upstairs. Mother was carrying a basket of laundry, and followed me down the hallway as I went to my room. The guestroom door was closed, and I assumed she was going to pack some of the things in the laundry basket. I was dead tired — my anticipation, plus the wine, had worn me down. I undressed, throwing my things in the laundry hamper and putting on my gray pajamas and nightshirt. I played back Ms. Hunter‘s comments in my head.


Chapter Thirteen — Goodbye In Blue Silk

I woke fairly early and lay in bed thinking about the start of my holiday and the pleasures that were awaiting me. But I dwelled on the last few weeks, and especially the last few days. My own mother was encouraging me to crossdress — the soft and feminine sweaters and such she had bought me, the lotions and perfumed soaps in my bathroom, our movie nights with me in my silk charmeuse set, the moonglow blue sand-washed silk, and mother in her nightdresses. And, of course, the dressing she gave me two days before, then having a romantic dinner with her and Mimi while dressed most femininely in creamy rayon slacks and soft sweater, the only piece of boys clothing being my loafers. And then having me dress in the beautiful blue silk surah pajamas for our movie night,

Full of anticipation, I showered and donned my gray cotton pajamas and nightshirt, including the bikini panties and camisole beneath. I was becoming rather creamy — both because of my thoughts and of my abstinence.

My revelry was broken when mother knocked on my door. She was already dressed in a gray jersey wool suit with a pretty blouse made of a brown and black georgette lace streaked with gold threads and a ruffled portrait collar.

"Good morning!" she said cheerfully. "Why don‘t you come down and have a little breakfast with me?"

She waited for me in the hallway. I threw on the cotton robe and stepped out. The door to the guestroom was still closed, but I didn‘t think anything of it. We went downstairs together.

During breakfast, she said "You know, sweetie, before Mimi comes to pick me up in an hour or so, I was thinking that maybe we spend some time together — after all, I‘m going to be gone for a month."

"Uh, sure… What did you have in mind?" I asked with a little trepidation.

"Well… you know those blue pajamas you wore the other night? I never had a chance to really see you in them — you were all covered up in your new robe. Would you mind putting them on for me?"

"Okay, if you‘d like me too, mommy" I replied willingly. What a great way to start my holiday — dressed in the silk surah set at my mother‘s request.

"Oh thank you, Evelyn! You‘re so wonderful and special. Let me go get them — and then come to my room; the guest room is a bit of a mess…"

She disappeared upstairs rather quickly. A minute or two later, I heard her call "Evelyn?" from the top of the stairs.

"Coming, mommy" I called back.

She met me at the top of the stairs and we walked together to her room. Draped across the armchair in her room was the set — pajamas bottoms, tap panties, short chemise, matching short robe, the matching bikini panties, and the pantie girdle. She had taken the garter clasps off the pantie girdle and placed them on her nightstand.

"Why don‘t you slip into these, dear, while I finish some last minute things in the guestroom and take my bags down."

I offered to help her with her bags, but she refused, saying she could handle it easily.

Tingling all over, I undressed and almost breathlessly slipped into lovely blue silk and white Venise lace. I had barely finished dressing when mother knocked. I left the short robe untied for I knew mother would ask me to untie it anyway.

"Are you dressed, dear?" she asked.

"Uh-huh."

She opened the door and, smiling broadly, came over and gave me a hug. "You look so nice dear. How do they feel?"

"Nice, mommy… the fabric is nice…" I mumbled.

"It‘s very fine silk, dear… the finest. It‘s meant to feel nice against your skin. Come and sit down at my dressing table and I‘ll brush out your hair."

As I sat, she told me, in a whispered voice, that I should let Mimi see me in the set. "After all, dear, she saw you the other night in them, and she was disappointed that you stayed wrapped up in your robe."

"Are you sure, mommy?" I asked in a whine, adding "I‘m not sure she should see me like this."

"I‘m sure dear. Just relax and don‘t worry about a thing, alright?"

She quietly brushed my hair then tied it back in a loose ponytail with a narrow foot-long length of white silk.

"Would you like to try on some of my jewelry? I think my lapis things would be so pretty with the set."

Soon she was helping me with her gold and lapis necklace, bracelet, and teardrop earrings.

"Oh… mommy… I don‘t know… aren‘t you going a bit overboard?" I asked quietly.

"Please, dear? It means a lot to me."

"Well… alright…" I whispered.

"Your skin and lips are really dry, dear; this dry weather is so bad for your skin" she said as an excuse to apply some moisturizing foundation and neutral lip gloss.

"I hope you‘ll be okay while we‘re gone, Evelyn. I guess I am a little concerned about what you‘ll be doing with your free time. I hope you‘re not planning on having any wild parties or anything like that."

"No mommy, nothing like that" I said a bit defensively.

"Oh, good; I didn‘t think you would. If you‘re bored dear, and need something to pass the time, well… there are all those things that Beverly has been sending me and, of course, there‘s the things in my closet."

"Oh… okay, mommy. I might do a little bit of… you know… if that‘s okay."

"Of course it‘s okay, dear. Please do."

I had goose bumps all over — mother was practically pleading with me to dress-up on my holiday.

She waited a moment then said "Can I bring out your eyes with a bit of mascara and powder? Just a bit?"

"Okay" I whispered.

She applied brush stroke or two of blue eyeshadow. Without asking, she used her big makeup brush to dust on a tad of blush.

"I sent in those pictures we took on Thursday. They should come back Tuesday or Wednesday, so watch for them. You can put them somewhere in my room, alright?"


We both heard a noise downstairs — Mimi letting herself in. "I think Mimi‘s here. Come along, darling, we‘ll have a little visit before we go."

I wrapped the robe around me, hoping to hide the lacey camisole. It really didn‘t matter -- the robe was profusely adorned with lace as well, so I wasn‘t hiding anything. But it did mostly hide the necklace. Mother gave me a pair of her white satin bedroom slippers to wear.

"Mommy? Are you sure about this? I mean letting Mimi see me like this?"

"Of course I am dear. Mimi said she really wanted to see you in the set. I think it‘s because she comes from a culture where it‘s fashionable for sophisticated and well-off boys to wear lace and fine things." She took my hand and squeezed it, saying "Come along dear. It‘s not like you‘re wearing a pretty dress and high heels like the other day — they‘re just pajamas.

I took a deep breath and sighed "okay…" I followed her down the staircase. Mimi was in the kitchen and mother led me to the living room couch without Mimi seeing me. Mother went to the kitchen and I heard her say to Mimi "…there‘s something I want you to see."


Mimi came into the room. She was dressed in a very nice black wool suit; an over-the-knee length skirt and a jacket, opened to reveal a white ribbed crew-neck sweater and a blue floral pattern chiffon scarf clasped with a gold scarf clip. She was wearing black pumps with a higher heel than she usually wore.

"Oh my goodness, Dahl" she said quietly. "Look at you. Such nice things… you‘re very lucky to have a mommy who likes having you wear such nice things."

They both sat down, mother next to me. Mimi left for a moment and came back with a pot of tea and cups, then sat on the chair facing us.

For the next ten minutes or so, mother stroked my hair, patted me on the knee, and gently rubbed my back as we chatted and drank tea. She drew back my hair to expose the earrings for a moment. She was coddling and cosseting and petting me and it was affecting me quite a bit. My robe loosened and the necklace was showing, and swung away from my neck when I reached out for my teacup. I had to reach and catch it, showing my bracelet, then adjust everything. I thought how I have looked; an effeminate sissy in lacy silk surah and satin slippers, wearing makeup and dangling earrings


"So, Dahl, are you going to miss your mommy?" Mimi asked.

"Of course" I replied, blushing at the use of ’mommy‘.

"Your mommy will certainly miss you, dear" added mother, picking up on Mimi‘s use of the affection. "Take good care of my precious while I‘m gone, will you Mimi?" she added.

"Oh, don‘t worry Ellen" replied Mimi. "I‘ll make sure that Dahl is well kept."

Mother‘s finger came to rest on the little buckle of my camisole strap and she let it dally there as she said "Make sure he gets plenty of rest, drinks his tea every afternoon and evening, takes his vitamins, and doesn‘t overexert himself — he‘s still not completely over his hepatitis." Of course I was completely cured and there was no need for mother‘s concerns, but I said nothing.

"Oh… and I think Dale wants to sleep in the guestroom while I‘m gone" she added.

Mimi smiled and said nothing.

"And you should take a nice nap there this afternoon, dear" added mother. "You got up early and I think you‘re still tired from yesterday."


It was time to leave. Mimi said she would return about noon the next day and would call beforehand. She had left me some stew in the refrigerator. Final goodbyes and hugs and kisses were made. I stood in the doorway, waving goodbye as they drove off.

I locked the door and let out a moan. Finally, the moment had arrived — the start of my holiday. I was so full of anticipation, so creamy. I knew that the creaming I would have in a few hours would be the best ever, and I wanted to build up to it nice and slow.

"Oh mommy…" I whispered, thinking of the morning and the last few days.


I decided I‘d go back to my mother‘s room and remove the pantie girdle and get properly made up. Then I‘d partake of a good bit of hashish and then enter the guestroom for a delightful, pleasure-filled morning and afternoon.

The first thing I did was to paint my finger and toe nails with mother‘s deep red polish. After my nails dried, I retrieved a daintie glove that I kept hidden away and went into mother‘s room. It felt good to get out of the pantie girdle and the daintie glove felt fabulous. No need soiling the beautiful panties.

Back in mother‘s room, I got properly made-up with mascara, dark eyeshadow, deep red lipstick and blush. Mother had a big blue chiffon hair bow which I fixed to my hair, taking off the white silk streamer. I slipped into a pair of her blue pumps, and then brought out my hashish stash.


Chapter Fourteen — Gifts In The Guestroom

I was really flying high. I minced and swished to the still closed guestroom door, the door to my boudoir where my mother said I‘d be spending my holiday and doing what my mother suggested — dressing up in ladies things.

I breathlessly entered the guestroom.


I gasped and let out a cry of delight — lying on the bed was the petal pink chiffon dress! The very one she had seen me admiring a few days before. It lay across the bed on a padded and scented satin clothes hanger.

Hanging on the dressing screen, also on padded satin hangers, was a set of daywear; camisole, pettislip, and dance panties. The camisole hung from hanger by its straps that were held in place by little faux pearl pins, and the pettislip and panties held by padded clasps attached to the hanger. They were muted lingerie pink with ivory Venetian point lace trim, with fancy ecru and gray embroidery, made with a delicious blend of silk, rayon, and micro-fiber. The label said ’Private Label Lingerie, New York‘.

Waves of emotions swept over me — my mother bought me the dress, the beautiful dress that she caught me admiring. There it was, draped across the guestroom bed — my boudoir - with a set of exquisite daywear hanging from the dressing screen, things she must have bought on her last trip to New York.

The bed dressing had changed as well. The bed cover was now a dusty rose, made of soft puckered cotton matelassé. The fitted corners had the most feminine effect; two wide blush pink satin ribbons ties, both tied in big bows. It took me a moment to see that the center of the bed cover had a large oval woven into it, and in the middle of this oval, monogrammed in large florid script, were my initials, ’EDF‘. There was a new pink satin balloon skirt around the bed as well. Two large bolster pillows that matched the bed cover now rested against the headboard; these too had an oval with my initials in the middle and a wide white lace hem. The sheets and other pillowcases were new as well — petal pink satin detailed with a picot trim of ecru and cream threads. Two cylindrical burgundy silk panne pillows with white eyelet lace and pink ribbons accents had been added to the bed clothing. Later, I found the original sheets and bed clothes had been neatly folded and placed in the linen closet of the guest bathroom.

Then my eyes wandered to the loveseat. There was an opened gift-box with pink tissue parted to reveal a mound of lilac chiffon and white Alencon lace. It contained a lilac peignoir and robe set, the peignoir with an empire-waist, tied with a wide, glimmering white duchess silk ribbon, the square-neck bodice all white lace, the graceful and fluid skirt a sheer lilac chiffon. The full length robe was of the same fluid lilac chiffon, with Alencon lace lapels and wide bands of lace at the sleeves. Then a pair of all-lace bikini panties, tied at the side with lilac ribbon, and a lilac chiffon dance pantie, also tied with lilac ribbon. The label on the box said it was from a boutique called "Isabella‘s" and the label said "Private Label Lingerie", the same as the daywear set.

But the delights didn‘t stop there — on one wingback chair was a rather large package from Auntie — it must have been delivered the day before, I guessed. The box was opened, but the contents were untouched. On top was a heart-shaped white satin boudoir pillow, decorated with a profusion of lace with silk flower petals and long ribbons of pink and blue pastels. Beneath it was a short chemise, antique white Chantilly lace over white silk charmeuse and a matching tap pantie, the same Chantilly lace over white silk charmeuse. Both items had blue piping, the chemise tied with a matching blue cord, as was the waist of the tap pantie. As I lifted these delights out of the box, there beneath it was a brassiere, garter belt, thong, and bikini of the same Chantilly lace and blue piping. It took me a moment to realize that they perfectly matched the robe and pajamas that Auntie had given me — the piping was exactly the same and they were the same label. Next, a two-piece; long two-tiered chiffon skirt, pink and red roses and lilac against an ivory background, with a matching asymmetric hem long bell sleeve tunic top and long matching chiffon scarf.

Beneath the dress was a risqué foundation set of pink satin and shimmering gray lace — a full-cup brassiere, a waist cincher, bikini panties, and tulip panties. And beneath that was a short robe to match. The labels said they were made by Diki. They would go well with both the daywear set hanging from the dressing screen and even the gray jacquard daywear set Auntie had sent earlier. Then beneath that was yet another foundation set! — White crepe de chine with white lace flecked with pink and blue — it matched the Jane Woolrich chemise and dance pantie that I was wearing at that moment. Then three delightful silk and lace tulip panties — white, pink, and baby blue. There were packages of real French heel silk stockings in blue, black, pink, and white; and pairs of opaque cotton and wool blend stockings in black, brown, and white. The final things were a bit of a surprise; two dozen damask handkerchiefs bundled with a pink ribbon, each identical, trimmed with fancy ecru Swiss lace. I had seen them for sale at the Gilded Lily. They were unusual because they were hexagonal rather than square, meant to be stuffed into a breast pocket. I couldn‘t figure why they were included in the package. Then a possibility came to me — they were meant as pantie napkins. I flashed back to the evening that Auntie and Suzanne had dressed me and how I cut apart a linen hand towel to use as a pantie napkin — perhaps they discovered the two halves and put two and two together, realizing that I had used it to protect my panties. Whatever the reason, the handkerchiefs were perfect for that purpose; the damask was thick and quilted and the hexagonal shape would form and fold easily around my daintie.


Neatly folded on the other wingback chair was a lightweight off-white ribbed turtleneck made of oh-so-soft angora, mohair, and merino wool blend. It was a true turtleneck in that the neck had to be rolled over itself. Unrolled, it reached to my eyes. Draped over the arm of the chair was a delicate open-weave sweater, the color soft dove gray, knitted of cloud-soft alpaca wool. The design was unusual — a surplice wrap, open to the waist, with full sleeves. At first, I thought it was a pullover, but realized that it was a true surplice wrap, with long lengths of yarn used to tie the waist. Draped over the back of the chair was a pair of wool jersey slacks, charcoal gray with white pinstripes. They had a front zipper, high waist, and full legs. On the floor at the foot of the chair was a pair of suede charcoal gray kitten-heel pumps, banded with thin decorative black satin.

I turned my attention from the box to the vanity. There was a crystal vase of fresh-cut roses, a crystal champagne flute with a pink and white lace ribbon tied around the stem, and a cut-glass perfume bottle with a tasseled squeeze bulb atomizer, filled with perfume. There was a new porcelain figurine by Santini of a lady at her dressing table putting on stockings. It was a rather erotic figurine.

In the middle of the vanity top was a pink chiffon hair bow with a cluster of ivory organza flowers in the middle of the bow and several descending thin ribbons streamers of pink and ivory — a perfect accessory to the pink dress. And in front of the bow were two black velveteen jewelry presentation boxes. I opened the larger one to reveal a fine three-strand pearl necklace, three-strand pearl bracelet, and drop earrings; several pearls suspended on a delicate gold chain. It was the set that mother and I admired together at the jewelry store where my ears were pierced. I knew how expensive this set was — almost three thousand dollars! The smaller box contained the antique silver filigreed hairclip from the same boutique. I went through the drawers of the vanity and found new items; bottles of pink and red nail polish, a bottle of nail polish remover, an opened bag of cotton balls, a couple of dozen triangular sponges, another gift box of makeup with powders in hues of pink and lilac, and a glossy book "Secrets of makeup". I noticed that in the refuse can next to the vanity were the plastic seals that fit the nail polish, the triangular sponges, and the gift box.


I opened the closet. The first thing I noticed was a dozen or so empty padded satin hangers, each with its own perfumed lace sachet hung from the hook. The cloth garment bags over the furs were now gone as well. There was a new knit sweater jacket; off-white, mid-thigh length, medium weight, with a shawl collar, hood, and a self-tie belt. The yarn material was synthetic — orlon and nylon — with flecks of tan, peach, and brown to give it a bit of a tweed effect. The overall effect was slightly androgynous. At the bottom of the closet was new pair of pink and cream two-toned pumps with a two-inch Sabrina heel, a pair of neutral ecru-colored patent leather oxfords with a high Cuban heel, very cute and feminine, a pair of blue velvet boudoir slippers with gold thread embroidery, and another pair of white satin stiletto-heeled boudoir slippers with a big puff of marabou on the instep. I put on the boudoir slippers. The shelf contained a clutch purse that matched the pink and cream pumps.


Titching with pure sensual delight, I opened the bureau drawer where the foundations were kept. The blue stockings, the ones with the run, were gone; they were replaced with a new package. There was also a pair of plain white cotton stockings. Then another set of foundations in shiny pewter gray satin; brassiere, a waspie style garter belt, and a pair of precious tulip panties. All three pieces were decorated with blue embroidery and trimmed with matching pewter gray cut lace. The set was made by Wacoal and would go perfectly with the silver gray Natori daywear. The thought occurred to me that mother must have realized I had worn her gray foundations soon after the Natori set arrived from Auntie, and decided that I needed my own set to wear with the daywear. Then I discovered the sachets that I used to provide padding beneath my brassieres. Looking further, I found a white satin bustier, the torso portion made of sturdy elastic fabric, the all lace breast cups were padded, with a low back and removable shoulder straps. The bottom had deep scallops to accommodate four wide satin suspenders.


But then I noticed something else. Peeping out from the pink chiffon dress was a pink envelope. I gently pulled it out from beneath the dress. I was addressed to "Evelyn" in my mother‘s handwriting. My fingers trembled as I sat down at the vanity and withdrew the letter inside.

My Dear Evelyn:

These things are for you, my dear. I want you to have them and to dress in them.

I know you probably don‘t understand the feelings you have about dressing up, but I think that I do. You have had to grow up without a father and with a mother who wished you were her daughter, a daughter with whom she could share her love of fine feminine dresses, soft furs, jewelry, and loungewear. Under these circumstances, how could you not have feminine desires, dear? You are such a delicate and precious boy and I watched with joy as you discovered your feminine side. And then when I finally had the courage to dress you the other day, I was delighted to see how perfectly beautiful you are, so pretty, and how you comported yourself with such feminine grace.

I hope that while I‘m away, you‘ll take the opportunity to dress in all these lovely things that I so enjoyed picking out for you these last few months, as well the things that your Auntie is sending to me. I hope that when I return, you have embraced your femininity and you and I can begin a wonderful relationship, going out together as mother and daughter, sharing experiences together.

You need to know that Mimi is aware of all this. She adores you and understands your feelings. She is very supportive and said that she‘d love to help you become comfortable dressing as a lady. If you want her to help and assist you all you have to do is ask her, or, if you‘re uncomfortable with that, dear, just dress in something soft and feminine as a sign you want her to help you. I do hope you‘ll let her help you.

Take care, my dearest. I‘m so looking forward seeing you when I return.

Love Always,

’Mommy‘

PS: I‘ll call you when I get to Europe, unless it‘s an emergency

I was just stunned. She (and Auntie, too) were lavishing me with expensive and exquisite things to dress in, absolutely spoiling me with stunning lingerie and dresses and sweaters and, oh yes, a very expensive set of pearls. And the way she had signed the letter ’Mommy‘ with quotes around it. And then there was the matter of Mimi. Was my nanny going to be dressing me?

I arranged all the mirrors just so, having turned the dressing screen so that its mirrors faced the bed, the ottoman in front.

What a tantalizing, sensuous morning and afternoon I had! I disrobed and applied the scented dusting powder and slipped into the Jane Woolrich chemise, dance pantie, and robe. I thumbed through the "Secrets of makeup" book for pointers, then applied pink nail polish to match the pink chiffon, then changed my makeup to softer hues suited to the pink chiffon. I swept my hair back and clasped it with the pink chiffon bow. I paused to heighten my senses again with the hashish. In the bathroom, I discovered new bottles of expensive aromatic bubble bath, lotion, and bars of perfumed soap. Completely and deeply into my feminine self, I donned the pink and gray lace foundations from Auntie and the delicate daywear set from mother and the pink and gray short robe from Auntie, titching the whole time. I almost swooned while drawing on the new pink silk stockings. Heels and my new set of pearls followed. Oh, what a rich little spoiled sissy! I paused in my dressing and wandered downstairs for a snack in my lingerie, robe, heels, and pearls to discover a champagne bottle in wine chiller that had a big pink and white lace ribbon bow on it, just like the champagne flute in the guestroom.


Back to my boudoir to finish my dressing, sipping on champagne, listening to romantic classical music, safe and secure and knowing that mother and Auntie and Mimi were giving me their approval. I almost fainted when I finished donning the pink chiffon dress. The mirror reflected a refined and coy young lady, all pretty in pink. "Oh mommy…" I moaned. "Oh Mimi… are you going to make me wear dresses?"

I tried to delay creaming as long as possible, but by mid-afternoon, my daintie was absolutely aching, all moist in her protective cashmere glove. I stood at my mirrors; my senses heightened by the hashish, a little tipsy on champagne, titching, whimpering, and saying my O‘s.

The thought struck me that my creamings purged me of the awful boy hormones that were welling up inside me. How perfectly natural, I thought. By purging myself of these despicable hormones, I would naturally become more feminine. And what better way to elicit a deep purging than by dressing up in fine lingerie, pretty designer dresses, flirty high-heels, expensive jewelry, scented dusting powders, expensive perfumes, fine accessories and decorations, and all made up, my hair coiffed? It all made perfect sense to me.

My cries reached a crescendo. I lifted the dress and pettislip to reveal the beautiful panties and moved my leg just so. As the precipice approached, I was crying out ’Oh Evelyn‘ and ’Oh mommy‘. Then my oh-so-stimulated daintie convulsed. The whole room seemed to contract and expand with each withering gush… Oh how I gushed! I collapsed on the bed.

Fortunately, only my bikini panties and dance panties were sullied — it would have been disastrous if my cream touched the exquisite chiffon of the dress.


That evening, I was dressed in the lilac chiffon peignoir and robe, the white fox stole around my shoulders. I had laid the mink throw on the bed with several of the silk brocade pillows. I had a long, slow, delicious cuddling on the pillows, kneeling over them, watching myself in the mirrors, my silk stocking‘d legs resting on mink, the chiffon puddling around me, my daintie wrapped in a silk scarf. But I had drunk too much champagne and wine…


To be continued…

The Awakening of Evelyn - Book 4

Author: 

  • Evelyn D. Fairechild

Audience Rating: 

  • Adult Oriented (r21/a)

Publication: 

  • Novel Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

Other Keywords: 

  • lingerie
  • Petticoats
  • Soft Sweaters
  • Boudoir
  • Oh well

Permission: 

  • Posted by author(s)

The Awakening of Evelyn

Book 4

Evelyn D. Fairechild


Under the tutulage of Mimi, Evelyn's journey begins

Chapter Fifteen — The First Week Of My Holiday

Sunday

I awoke in the guestroom, dressed in the exquisite new lilac chiffon empire-waist peignoir, robe, bikini panties and dance panties that my mother had gifted me. The room was a mess. I was a hung over — I had a little too much champagne the evening before. I couldn‘t even remember if I had creamed the previous evening, but the way I felt told me I hadn‘t.

The first thing I did was to reread the letter from mother, especially the part about Mimi wanting to ’help‘ me:


"You need to know that Mimi is aware of all this. She adores you and understands your feelings. She is very supportive and said that she‘d love to help you become comfortable dressing as a lady. If you want her to help and assist you all you have to do is ask her, or, if you‘re uncomfortable with that, dear, just dress in something soft and feminine as a sign you want her to help you. I do hope you‘ll let her help you."


Mimi was to arrive in a couple of hours and I had a number of things to do, such as tidying up the guestroom and deciding how I should dress for her. I threw on my terry cloth bathrobe and had a quick breakfast, thinking about how I wanted the day to unfold.

My relationship with Mimi was, of course, much different than my relationship with mother. Mimi was both a kind of nanny and a surrogate aunt. My mother, like me, avoided confrontation, but Mimi was more direct. By softly dressing as mother‘s letter suggested, I knew that Mimi would confront me about my crossdressing. I was in a complete tizzy trying to decide if I wanted to go through with what my mother had suggested. Mimi wanted to help, but how? What would be her reaction? Maybe she told mother one thing, but was going to do another?

All these questions raced through my mind as I finished breakfast and headed back to the guestroom.

I took a shower and applied after bath body lotion and powdered with scented talc. I then slipped into the wrap that matched my bathrobe.

My next task was to tidy the room. I had a lovely time putting away all the dresses, foundations, lingerie, and night dressings that were scattered about. It put me in a really ’creamy and dreamy‘ mood, where my daintie was in a sort of stimulated limbo state, small amounts of cream keeping me all moist, an exquisite mesmerizing ache, and my eyes dilated for that dreamy time-to-go-to-bed look. I began to resent the fact that Mimi was coming over — I was in the mood for a long luscious purging.


My mood made it easy for me to decide and dress "…in something soft and feminine as a sign…" as mother had written. I just couldn‘t imagine any other outcome.

I was in a trance-like state, going through the motions as I donned the new silk charmeuse foundations that Auntie had sent, the ones that matched my pajamas and robe, along with the damask lace-trimmed handkerchief as a pantie napkin, the lovely matching chemise and tap pantie, and the pair of white silk stockings that Auntie had also sent.

I decided to wear the ensemble that mother had lain out on the wingback chair. It seemed to be beckoning to me — something "soft and feminine" to wear for Mimi. Could it have been that mother gave me the ensemble expressly for this occasion? And so I dressed in the off-white mohair, angora, and merino wool blend turtleneck sweater, so very girlish and feminine with its delicate strands of angora and mohair decorating the fur and its voluminous rolled-over turtleneck. The charcoal gray wool jersey pinstripe slacks were next; they fit perfectly, the high waist and full cut legs so very alluring. I slipped into suede charcoal gray kitten-heel pumps, and evaluated my ensemble in the mirror. The sweater hid the high waist of the slacks, and the hem of the slacks covered the kitten heeled pumps while standing. But I could distinguish the camisole beneath the turtleneck, but just barely. So I donned the delicate dove gray surplice wrap alpaca sweater — it was just so very soft and pretty and it left absolutely no doubt that I was crossdressed. But it did hide the camisole beneath.


I sat at my vanity and selected the small gold hoop earrings that mother had bought me and pulled my hair back in a loose ponytail with the tortoise shell hair clip. I applied just a bit of foundation cream, smoothing it in with the triangular sponges, just as the ’Secrets of Makeup‘ book had prescribed. I followed with a very modest application of eyeshadow, blush, and lip gloss; a bit more than what I was wearing the previous morning when mother dressed me in the blue silk surah. My eyelashes had already been accentuated from the mascara I had applied the evening before.

I stood at the cheval mirror again and evaluated myself. What a girlish, softly sweater‘d sissy I was! "Eww…" I moaned. "Mimi? Is there something you want to discuss with me?" I said to the mirror in anticipation of whatever was to pass that afternoon. I continued with my little lisping soliloquy, saying "Mommy says you want me to wear dresses and stockings and high-heels and pretty underthings… She says that you want to help me dress as a lady…"

With serendipitous timing, she telephoned as I was reveling in my shameful soliloquy.

"Good morning, Dahl" she began.

"Good morning, Mimi. How are you?" I replied sweetly.

"I‘m fine dear. I‘m back. I‘ll be over there in about an hour."

"Wonderful, Mimi" I replied without hesitation.

"Then I‘ll see you in a bit. Perhaps you could make some of your special tea and set the table for lunch. I‘ll bring us a nice lunch and then there‘s something I want to discuss with you."

My heart skipped a few beats as I let out a silent moan, watching my reflection in the mirror.

"Yes, Mimi" I replied with just a bit of soft lisp.

We said our goodbyes and I hung up the phone.


After checking myself for the hundredth time, I went downstairs, started a pot of my special tea and then set the table in our formal dining with our best china, silverware, crystal water glasses, and tea cups.

I nervously waited for Mimi, checking and re-checking myself in the mirror, finally noticing my fingernails were still painted pink. I was just about to go upstairs and remove the polish when Mimi arrived. She was nicely dressed, this time in a floral pattern skirt against a deep blue background and a claret red cashmere twinset with a necklace of big carved ivory-colored beads.

I was standing with my back to the dining table, leaning against it, my hands behind me to hide my pink polished nails, one leg slightly bent. With a quavering voice I greeted her.

"Hello Mimi, how are you?"

"Hello Dahl. I‘m fine, thank you. My…" she said, looking me up and down "…but you look very nice; such soft and pretty sweaters." She glanced into the formal dining room and said "You did a very nice job setting the table, dear. Come, let‘s put out the lunch I brought — I‘m hungry." She had picked up lunch from our favorite Japanese restaurant.

Without much ado, we served ourselves. Mimi got out my vitamins and had me take them before sitting down. "After lunch, Dahl, there‘s something you and I need to discuss, isn‘t there? But for now, let‘s just enjoy our lunch."

She managed to find something to talk about during lunch. At one point, I gave a little yawn. "You look tired, dear" she said. "Did you sleep well last night?"

"No, not really" I replied. "I guess I‘m a little tired. I‘ll probably take a nap later today."

"I think you should. As your mother said, you need your rest."


Lunch was finished. I excused myself to the bathroom and watched myself in the mirror as I drew down my slacks and panties. ’This is it‘ I thought to myself.

When I came out a few minutes later, Mimi was in our parlor, sitting on the couch. She patted the seat next to her, saying "Come sit with me, Dahl dear."

I sat down, knees together, my head bowed, my hands folded in my lap, almost quivering. My slacks revealed the kitten heels and white silk stockings. Mimi gently placed two fingers underneath my chin and raised my bowed head. She took my hand gently in hers.

"Dahl dear?" she started, looking me in the eyes. "I know you like wearing ladies things, and that you like to dress up as a lady, just like you are now. You are wearing ladies things, aren‘t you?"

"Yes, Mimi" I replied, my eyes tearing up. There was a box of tissue on the coffee table. Mimi withdrew a tissue and handed it to me. Wordlessly, I dabbed my eyes. A bit of mascara came off on the tissue.

"You‘re wearing ladies underthings, too, aren‘t you?"

"Uh-huh."

"And you‘ve polished your nails, I see."

I sniffed.

"Your mother and I have discussed this. She has known for some time, as have I. I‘m glad it‘s finally out in the open. She dressed you in a pretty dress a few days ago, didn‘t she?"

I bowed my head and blushed. My ears were ringing. Again she put her fingers beneath my chin and raised my head.

"She said you looked beautiful. I‘m sure you did. You look very pretty right now. And you enjoyed it, too, am I right? …having your mommy dress you? You really liked being dressed as a fine young lady, don‘t you?"

"Yes, Mimi" I breathed.

"You should not be ashamed, Dahl. I think that it‘s wonderful you discovered yourself." She was searching my eyes as she said this. She held my hand in both of hers and continued, pausing occasionally to let her words sink in.

"As I told your mother, I am happy to help you become comfortable dressing up as a young lady, to get beyond your furtive little dressing-up episodes — you‘ve had a few of those, haven‘t you?" She didn‘t wait for a reply, but continued with "Your mother hoped that while she was away, you would overcome your inhibitions about dressing as a girl around us. When she gets back, she wants you to be as much at ease dressing up around her as possible because… because she would like to start taking you out as her daughter."

She paused for a long moment, then lifted my chin again and looked me in the eyes.

"So, my dear child, I just need to make sure. Please tell me — do you want me to help you?"

"Yes Mimi, I do" I blurted out, dabbing my tears again.

"Good!" she said, smiling broadly. "I was hoping you would say yes — not that it would have mattered much." She gave me a hug and stroked my head gently, saying "It will be all right, Dahl, you‘ll see. I‘m really looking forward to helping you — it will be fun; doing something I‘ve wanted to do for some time. It makes me feel young, like when I used to babysit you… Don‘t cry; dry your tears, mon chéri…" She hadn‘t called me ’mon chéri‘ in years.

She continued to stroke my head. I gathered myself together and sniffed back the tears.

"So… Dahl?" She continued once I had gathered myself. "I have decided that you should dress as a lady whenever you are home. This, of course, is the first step for you to become more at ease. And I‘ll be here to make sure you are dressed. And I have thoughts about other ways to help you as well, but let‘s just leave those ideas until later, all right? But I want you to first agree and promise that you‘ll dress up as a young lady whenever you are home."

"Okay… I mean… I mean unless somebody else is here, someone that knows me…" I trailed off.

"Of course dear; but you‘re not planning on inviting any of your friends over, are you?"

"No, Mimi" I replied.

"Neither am I. So it‘s agreed, then?"

"Yes, I agree, Mimi. Yes… thank you" I replied with relief, joy, and newfound confidence, adding "I promise to dress up as a young lady whenever I‘m home."

I bowed my head as my words sunk in. I realized just how lucky I was and how very kind Mimi was. With a shaking voice, I thanked her, saying "Oh Mimi that sounds wonderful. Thank you so much, Mimi. Thank you for helping me."

"Of course, my dear child… You‘re welcome. And you‘ll be staying in the guestroom, won‘t you? It is very lovely and feminine, isn‘t it?"

"Yes it is, Mimi."

"Your mother decorated it just for you, you know."

"No… well, I wasn‘t sure" I replied.

"Now… what does your room look like? Did you put away all the things your mother laid out? And how about the package from your aunt?"

"I put them away, Mimi."

"Good for you, Dahl. Now, I would like to go tidy up the guestroom. I want to make sure that everything is in its proper place since you‘ll be staying there and I‘ll be taking care of it. You can put the dishes away and then I want you to go and unpack my car and bring my things into my room. While you‘re doing that, I‘m going to select something for you to wear for the rest of the afternoon. I need to leave for a while so I can drop by my office and go the grocery store. It will take me a few hours. While I‘m gone, I think you should take a nap and then dress yourself properly for dinner, alright?"

"Yes Mimi, thank you."


She rose from the couch and went upstairs. I sat for long moments, a thousand thoughts and questions racing through my mind. But mostly I felt relief — it was all finally out in the open. I rose from the couch and stood in front of the large mirror hanging over it, and just looked at myself for a while, thinking about what Mimi had just said.


I put the dishes away then went to Mimi‘s car. In the trunk were two large suitcases, a couple of cloth bags with toiletries and shoes. In the back seat was clothing on hangers. She had brought two nice dressing gowns; one a green tartan in very fine combed wool, the other her deep blue checked jersey. Next were three ballet dress nightgowns; the elegant and flattering black one I had seen her in before and two others, identical except for their color: claret red and creamy off-white. Although Mimi wore them as nightgowns, they could just as easily be worn as day dresses. Then came various outwear: a pleated royal blue skirt, a pleated heather gray skirt, her black wool suit, a long black rayon skirt with attached self-tie waist sash, two identical rayon blouses with slightly puffed shoulders, lace band collars, and lace accents on the sleeves; one in white, the other in pink. Both blouses had long and wide detachable neck scarves with big bows.

To my surprise, she had brought cocktail and eveningwear as well; a flattering cerulean blue surplice wrap jersey cocktail dress. a deep blue chiffon column gown with a wrapped and knotted runched bodice and cap sleeves; her silver blue chiffon palazzo slacks matched with a beautiful beaded blue bustier and a sweeping silver blue chiffon jacket embroidered with blue thread; a drop-waist pink silk Peau de Soie gown with a draped neckline; and a black lace cocktail dress with a red belt. Finally, there was a fetching black lace empire waist negligee. Was this something Mimi was planning on wearing in my presence?

She appeared downstairs as I was finishing putting her things away. I told her that she had beautiful things, and commented on the eveningwear.

"Those were gowns I wore when I did some modeling for that bridal magazine spread, remember?" I remembered— mother had gotten Mimi some modeling work, doing a high-quality magazine spread wearing mother-of-the-bride gowns. These were the gowns she wore.

"I decided that if you‘re going to dress up in pretty things, you‘d like some company. Besides, I‘ve hardly worn these since the shoot, and thought I could join in the fun, too. I‘ve got a few more at home. Perhaps I‘ll bring them later."

"Now, about your room, dear" she said, sitting down on the couch. "Your bed is made and turned down. And I put out a dressing for you to wear this afternoon and evening. I rearranged a few things as well. Now you should go upstairs and take a little nap while I go to the office and store."

"Yes Mimi. And… and thank you Mimi… thank you for everything" I said in a quavering voice.

"Come sit and give me a hug, dear" she said, smiling, patting the couch next to her. She opened her arms as I sat and I was soon enveloped in her breasts. She kissed me on both cheeks, and, letting the hug end, said "I can‘t wait to see you as a young lady, mon chéri. Just so there‘s no question…" she whispered, a reassuring smile on her face "…I want you to pad your bra, alright?"

"Oh… okay, Mimi" I replied, blushing.


Mincing on my kitten heels, I went upstairs to see what Mimi had chose for me to wear for the afternoon.

I could barely breathe as I opened the door to my boudoir. The bed was invitingly turned down, and draped across it were the De Pledge negligee, short robe, and tap pantie.

I sighed with delight as I stepped inside, taking stock of the room, catching a glimpse of myself in the mirror, so very softly sweater‘d, so very girlish. Hanging from the dressing screen were the charcoal gray knee-length fit-and-flare pleated skirt and the coordinated cashmere and mohair V-neck argyle sweater. On the floor were the black velvet pumps.

I glanced behind the dressing screen. The shimmering silver gray jacquard camisole, pettislip, and matching tap pantie hung from the back of the screen, each on their individual padded satin hangers. The ottoman was decorated with delicacies: the pewter gray embroidered satin brassiere, waspie and tulip panties, and the pair of opaque black stockings; all neatly placed as if for a display in a boutique window. I felt a little faint when I saw, next to the brassiere, the two sachets I used for padding brassieres. She must have known that mother had me pad my brassiere with them.

I stood in rapture, thinking about Mimi‘s choice of my afternoon dressing. I decided that it was perfect — casual and stylish, not too feminine (except, of course, I was a boy about to dress in them).

I inspected the rest of the room, first opening the closet to discover that everything had been carefully placed, loungewear on the right, daywear sets in the middle, dresses on the left. In the bureau, Mimi had gone through the drawers and rearranged things, including all my foundations.

After checking that Mimi had left, I started to undress, titching the whole time. I was down to my foundations and oh-so-aroused, about ready to dress in the lovely blue silk surah and white lace tap panties, negligee, and robe that Mimi had laid out. But I had a little problem — I had laundered all my daintie gloves and they were still wet (I had hung them to dry in a place where it was highly doubtful that Mimi would find). I couldn‘t possible sully the beautiful silk surah panties or negligee, but I so wanted, so desperately needed to cream while wearing them. However, I had an alternative; mother‘s scarf drawer was divided into two sections: one section for her favorite scarves and another smaller section for ones she hardly wore. It was in this latter section that I retrieved a pretty beige scarf made of a polyester chiffon material. I had seen her machine wash it once after she spilled some wine on it. If it could take machine washing, then perhaps… Minutes later I was standing by my bed, dressed in the exquisite silk surah negligee, robe, and tap pantie. Beneath my panties, I had wrapped my mother‘s beige chiffon scarf around my daintie. I carefully slid into bed, taking the bed covering that Mimi had turned down and slowly drawing it over me so that the weight of its folding rested against my throbbing daintie. With the thumb and forefinger of each hand, I reached behind my head and gently clasped the corners of the pillow my head was resting upon. I began to churn ever-so-slightly beneath the weight of the bed covering, moaning my O‘s. A flood of emotions swept over me as I whispered "Oh Evelyn…" My toes tingled and curled as I glanced at my dinner ensemble that Mimi had hung on the dressing screen and I let out a cry as the waves and waves of pleasure inundated me and sullied my mother‘s scarf.


I managed to sleep for about an hour or so, then woke and slowly and carefully dressed, battling both the butterflies in my stomach and the deliciousness of the dainties I was donning. I had washed the sullied scarf of my mother‘s and hung it in the bathroom, and it was dry by the time I finished dressing; it looked fine and I put it my bureau drawer.


I waited downstairs for Mimi, building a fire in the fireplace, and setting the table.

The moment finally arrived; Mimi‘s car pulled up. I was sitting at the piano when she came in. She had changed her clothes and was now dressed in a blue skirt, a burgundy satin top with a pretty scarf, and blue pumps. I stood, tried to smile, and with a nervous laugh, turned around and asked "How do I look?"

"My goodness, Dahl, you‘re even prettier than I thought you‘d be. Your mommy was right — you are a very very pretty girl. That skirt and sweater look splendid on you. How do you feel?"

"Wonderful, Mimi, I feel… I can‘t describe it… I feel…" I searched for just the right thing to say and came up with "really peaceful and content."

"Good for you. That‘s how you should always feel, Dahl dear. If dressing as a girl makes you feel that way, then that‘s what you should do."

Her tone put me at ease. No recriminations, no judgments (other than I was pretty).

I helped her with the groceries and pretended to do some homework.


About a half-hour or so before dinner she suggested that I go to my mother‘s room and ’accessorize‘. "Perhaps a scarf tucked beneath your sweater, or another hair clip or bow, maybe some jewelry, too."

Alone in mother‘s room, I was able to reflect on the day‘s events as I experimented with some of mother‘s artisan jewelry and scarves, finally deciding on an off-white chiffon scarf tucked into the V of my sweater, appearing as if I had a delicate blouse beneath, a pretty artisan glass pendant necklace, and several bracelets.


Mimi let me have wine with dinner, but only after I had taken my vitamins. It helped loosen my tongue a little, and the conversation quickly turned to my crossdressing.

She told me the story of the blue and black gown, how much mother had enjoyed picking it out for me. She said that mother talked to her about it, and how they both agreed that she should lay it out for me to find.

"Does my stepfather know?" I asked at one point.

"That pig? Hell no. All he cares about is making deals and gobs of money. He doesn‘t care about you or your mother. Just promise me one thing, dear. If he ever leaves your mother, you and mother go after his money." It wasn‘t the first time I heard her curse or talk disparagingly about my father.

"Do you think my Auntie knows?"

"I don‘t know, but given all the lovely things she‘s been sending, I suspect yes. Your mother seems to think they‘re being sent for her and she just wants you to have them, but I‘m not so sure. It‘s interesting to me that both your mother and your Auntie think you should be dressing as a lady."

"I… I feel so ashamed sometimes."

"Don‘t ever feel ashamed for who and what you are. There‘s nothing wrong with wanting to wear nice things and be pretty. Why shouldn‘t you be able to dress nice and pretty? I mean, girls these days dress like boys. That‘s certainly not the way I was taught. Like your mother, we were taught as girls to dress nicely. But most of all, Dahl, you said it yourself — you feel peaceful and content when you‘re dressed as a girl. That‘s what life should be — peaceful and content."

"Mimi, I do have one favor to ask you."

"Of course, dear; what is it?"

"When I‘m, uh, dressed up, could you call me by my first name? Hardly anyone knows what it is, and I think it might be, you know…"

"Of course… Good idea Evelyn." She pronounced it as ’Evh-ah-lawn‘ in a gentle French accent.


She then asked some strange questions about the bathrooms at my school — did they provide privacy? I told her that the school library had a couple of private bathrooms and that I sometimes used them on my way between my two classes.

"Are they secure? I mean, do their doors lock?" she asked.

"Um, yea, they do" I replied quizzically.

"And there are private bathrooms at the library, right?"

"Yes…" I began to have a glimmer of why she was asking.

"And one last thing, Da… Evelyn; you don‘t see many people when you work at the library, do you? I mean, except for Melanie."

"Oh, maybe once or twice a day someone will come upstairs. And Melanie doesn‘t come upstairs unless there‘s a reason. Why are you asking me these things, Mimi?"

"Well, from now on, Evelyn, I think you should wear ladies underthings all the time. It will help you become more at ease. But I want it to be safe for you to do so — the only real issue is when you have to use the toilet, isn‘t it? You have private toilets at school and work, so it should be safe for you to do so."

There was silence for a few moments as I let her proposal sink in and think it through. Mimi was first to break the silence.

"Evelyn, can you think of a reason why you shouldn‘t wear ladies underthings all the time? And, of course, as we‘ve already discussed, when you are at home, I want you to always wear a dress. I have some other thoughts about helping you feel comfortable being a lady, but we can discuss those later."

I honestly couldn‘t think of a reason. I mumbled something about Wednesdays when I stayed after school for orchestra practice, and that just being at school longer meant more risk. She said she understood and that we make ’adjustments‘.

"So… It‘s agreed then, isn‘t it, Evelyn? You will wear ladies underthings from now on, correct?"

"Yes, Mimi" I replied sheepishly.


After dinner, I cleared the dishes. Mimi excused herself, saying "Let me attend to your room, Evelyn, and lay out your night dressing."

I was sitting on the couch watching television when she returned downstairs. She had me turn off the television and said "I noticed that your mother bought you some nice overnight moisturizing lotions. You should apply some each night just before you go to bed, Evelyn — it will keep your skin nice and soft."

"Uh, okay Mimi. That‘s good advice" I replied.

"A lady‘s nighttime routine is very important, Evelyn. I suggest that after you apply lotion to your legs you put on the pair of cotton stockings I saw your drawer; they will keep the lotion from rubbing off. And cotton is a natural fiber so it won‘t harm your skin overnight. It used to be that young ladies also wore long gloves to bed after applying lotion to their hands and arms. Did you know that?"

"No, Mimi, I didn‘t" I replied incredulously.

"Perhaps we can find you some. You also want to be sure to use the facial creams your mother bought to remove your makeup — soap is just too harsh and will dry out your skin."

"Yes… I kind of knew that, I guess."

"And you should always brush out your hair, as well. My mother used to tell me at least one hundred strokes of the brush."

"Really? That sounds like a lot!"

"It‘s not, really" she replied "but it really helps to bring out your natural oils." After a moment, she said "You should go upstairs now and begin your nighttime routine. I laid out that pretty new chiffon set your mother bought you, and the white cotton stockings that you could wear overnight. They should stay up overnight without garters… we‘ll see. But don‘t dress in them until I come up — just wear your bathrobe, alright? I‘ll come up and check on you in about forty-five minutes — that‘s about how long you should spend on your routine."


The bed was not turned down. But laid across it was the lilac chiffon and Alencon lace peignoir and robe set along with the matching dance pantie. The bikini panties were missing and I just assumed they were in the bureau drawer. The pair of white cotton white stockings that Mimi had mentioned was also laid out.

I undressed and put my underthings on the wingback chair, and then went about my ’nighttime routine‘, applying lotion all over my legs, arms, torso, chest, neck, and shoulders. I slipped into the plush terry bathrobe as Mimi had requested, donning the pair of white satin and lace panties from the bureau, then removed most of my makeup with cold cream.

I was sitting at the vanity, slowly brushing my hair, when Mimi knocked. She was wearing her fine wool green tartan gown. Her robe was open enough that I could see her creamy white cotton empire waist gown beneath. She was carrying a large knitted handbag that she placed on the loveseat.

"Are you all done applying your lotions, Evelyn?" she asked casually.

"Yes, Mimi."

"Have you been counting your strokes?" she asked.

"Sort of" I giggled "I lost count at seventy a little while ago."

"Here, let me" she said, taking the brush from my hand. She idly brushed my hair for a few strokes, and then cleared her throat.

"Evelyn, there‘s something I need to ask you."

The pause was long enough that I replied "Uh… okay, Mimi."

"Evelyn… do you still have problems with bedwetting?"

"What??? Of course not!" I blurted out. As a child, I had problems with bedwetting, and my mattress had a rubber sheet on top until I was eight or nine. Mother thought I should be wearing diapers to bed, but I had refused. But as I grew out of that phase, I became aware that I had a weak bladder — our family doctor dismissed it as an ’active bladder‘ and said it was nothing to worry about and just ’plan ahead‘. But when I was sick with hepatitis, a nurse suggested that mother purchase some disposable diapers and bed liners, explaining that in my weakened state, I might become incontinent. I didn‘t wear the diapers, but I did allow the bed liner to be placed on top of the mattress. While I didn‘t have any accidents, there were a few occasions when I caught myself, waking up just in time.


"Now don‘t be mad, Evelyn…" she replied somewhat crossly. "I just wanted to make sure. The last thing we want is for you to wet these beautiful sheets and bed linens, not to mention this exquisite nightgown, don‘t you think?"

"Of course not, Mimi" I whined, adding "I haven‘t wet the bed in years. You know that!"

"Well, I just wasn‘t sure" she continued, her voice somewhat offended. "But I‘ve been thinking dear, that the emotions you‘ve released might trigger a bedwetting episode — after all, bedwetting does have emotional roots."

"It won‘t be a problem, okay, Mimi?" I retorted with a huff.

"Don‘t talk to me in that tone, Evelyn. After all, I‘m trying to help you" she said, raising her voice. "You do want my help, don‘t you?"

"Sorry…" I replied sheepishly.

"Well?" Her pause was long enough that I realized she wanted a definitive answer.

"Yes, Mimi, I want your help" I whispered, my face red.

"That‘s better. So… just in case, Evelyn, I brought along some couche-culottes" she said matter-of-factly. The last word sounded like "koosh-coo-lots".

"Some what?" I asked, stammering.

"Couche-culottes… Sorry, that‘s French. I think in English its nappies."

"Oh" I replied. I just sat there red-faced, my ears ringing.

"I would like you to wear them tonight and every night for a while, until we‘re sure you won‘t be wetting yourself in bed."

"Mimi" I whined. But it came out wrong. Instead of sounding indignant, I sounded like pleading resignation.

"Good" she said, thinking that my whine was meant as resignation. "I‘m glad you agree — I‘m adamant about this and the last thing I need is any arguments from you."

"Oh" I replied. Her tone was aggressive and quelled the thoughts I had of refusing.


She took the large knitted handbag she had left on the loveseat and went behind the behind the dressing screen, coming out a few moments later with the handbag.

"Evelyn, I want you to go and put on the couche-culottes I laid out" she said, standing by the dressing screen, her arms folded in a defiant posture, and nodding towards the dressing screen.

I rose and walked toward her, my head down, slipped behind the dressing screen, and examined what she put on the ottoman.

First, there was a pair of simple soft cotton terrycloth pantie briefs, white, the wide elastic waistband supplemented with a wide drawstring closure. I picked them up and noticed that the inside of the crotch had a couple of sewn-in loops that held a thick pad covered with soft terrycloth. What was inside the terrycloth covering I didn‘t know, but I suspected it was something synthetic, designed to hold lots of water. The pad was removable, only held in place by the loops, and was about ten inches long, three or four inches wide, and about two inches thick. The pad obviously was meant to hold most of the water and wick it away from the rest of the panties.

Next was a pair of baby blue shiny satin nylon briefs with lace panels on each side. The panties were lined on the inside with clear plastic. The elastic at the waistband and legs was an inch or more wide and backed with puckered cotton. I suspected that both the width and cotton backing were extra protection against leakage.

"A friend of mine left these behind" said Mimi from the other side of the screen. "She had an operation that caused her to be incontinent for a while. Anyway, she, uh, had bought a supply of these and I ended up with them when she no longer needed them."

"Oh… okay" I replied. It seemed like a made up story, but I wasn‘t going to question her. I removed my panties and slipped on the cotton terrycloth panties; drawing them past my dainty and high up on my waist, and then tied the drawstring. They felt really nice; the bulky pad pulled tight against me felt, well, sensual. The terrycloth was soft and plush. The plastic lined nylon panties came next. The plastic was stiff and crinkly and rustled when I drew them on. They fit tight around my waist and legs but the front panel and sides were snug, but the bottom and back were loose.

"How do they fit, Evelyn?"

"Uh… fine, Mimi."

"Well, come on out then. I want you to put some more lotion on your legs before you put on your stockings."

I tied the bathrobe tight around me and stepped out. She motioned for me to sit at the vanity and she went to the bathroom shelf to choose a lotion for me.

I sat at the vanity, parting my robe and applying the lilac-scented lotion she had selected. As I did, she took the stockings and rolled them for me.

"I assume you know the proper way to put on stockings, correct, Evelyn?"

"Yes, Mimi, I do" I lisped softly. She watched as I carefully rolled the stockings up my legs.

"Good, you‘re doing it just right" she said.

She didn‘t give me much privacy, watching as I drew the stockings to the top of my thigh, revealing the satin nylon panties. When I was nearly done, she took the dance panties and peignoir behind the dressing screen. Without any instruction, I slipped behind the screen, removed my bathrobe, and donned the panties and peignoir.

"Very nice, Evelyn, such very nice things" she said as I came out from behind the screen. She was holding the matching robe and helped me into it.

"I‘ll be back in a few minutes, Evelyn" she said, taking my underthings from the wingback chair. "We‘ll have a bedtime sherry. In the meantime, you‘ll find some more things in the bag" she said, motioning to the knitted bag on the loveseat. "Find some space in your bureau for them, alright?"

The bag contained about a dozen of the terrycloth panties, an equal number of the pads covers, and about twice as many manufactured absorbent pads made of synthetic material with a moisture barrier. The bag also contained three panties identical to the ones I was wearing, except their color was white, pink, and black. It seemed that everything was new and never worn or washed. I found a place in the bottom drawer of the bureau for them.


When Mimi returned, she was carrying two crystal liquor glasses of sherry. I was sitting at the vanity, brushing my hair. She handed me a glass, then sat down in the wingback chair, sitting upright with her legs crossed beneath her long nightgown.

"Have you had a nice day so far, Evelyn?" she asked.

"Oh yes Mimi — it‘s been wonderful."

"Good. Now I want to wear the couche-culottes every night or when you take a nap. I‘ll be checking them for wetness and if I don‘t find any within the next week or so, then you‘ll have passed my test and you won‘t have to wear them anymore. Understood?"

"Yes, Mimi" I answered, with a bit of whine.

"Now, what ladies underthings do you want to wear to school tomorrow? I suppose we should pick out your school clothes as well."

She decided that I should wear the white charmeuse foundations and the matching chemise, and tap pantie, along with gray stockings. She laid these lovelies out on the ottoman. I followed her into my ’other‘ room to choose some outerwear. She told me that she didn‘t want me to dress in anything to school that would cause ’speculation‘ as she put it. Her criteria was first to hide my underthings and secondly not to wear anything rough or coarse that might abrade my underthings. Together, we choose a pair of dark corduroy slacks and an earth-tone brown Donegal knit crew neck sweater. I had a dove gray zip up hooded sweatshirt that I would wear over the sweater. My shoes were a pair of worn leather loafers. I appreciated that she didn‘t try to make me wear feminine outerwear to school, but I was a bit concerned about the sweater collection that my mother had created for me; the sweater that Mimi had selected was probably the least feminine of the collection and I wouldn‘t be able to wear it every day.


We returned to my boudoir and she turned down the bed for me. She had me remove my robe and slide into bed, then covered me up and tucked me in. It was only nine o‘clock, but she said I needed my ’beauty rest‘. She kissed me on the forehead and said "pleasant dreams, Evelyn" before leaving, draping the peignoir over the wingback chair and turning off the overhead light.


I lay in bed stunned by what Mimi had in store for me — making me wear ’couche-culottes‘ in bed (my, but I liked the way they felt, so soft and snug, the plastic all crinkly), and making me wear a full set of underthings to school. I had to use the toilet and entertained the notion of wetting my couche-culottes, but I couldn‘t bring myself to do so and used the toilet instead. Before drawing the couche-culottes back on, I wrapped my daintie with my mother‘s chiffon scarf. Back in bed, I had a nice long pillow ride, sullying the scarf for the second time that day.


Monday

Mimi knocked on my door early to wake me and came into my room a few minutes later, dressed as she was the night before. She had me go to the bathroom and remove the terrycloth panties so that she could inspect them. I came out with the panties and showed her that they were dry.

"Very well, Evelyn" she said. I thought I detected a bit of disappointment in her voice. "Did your stockings stay up overnight?"

"Umm, pretty much…" I replied. In fact, the stockings had slipped down a bit to just above my knee.

"Do you think you should wear a garter belt to bed then?" she asked.

"Maybe" I replied.

"We‘ll give it a try tonight, then" she said.


I went down for breakfast still wearing the negligee and robe. Back upstairs, I showered and scrubbed, making sure any last vestiges of make-up and nail polish were gone. I then dressed in the things that Mimi had chosen for me.

Mimi drove me to school, having changed into her pleated royal blue wool skirt and white cashmere twinset. At school, it drove me to absolute distraction to sit in class thinking about the lovely underthings I was wearing and that I‘d soon be home, wearing a dress and stockings and heels and makeup. In fact, Ms. Hunter asked me after class if I was ’okay‘ because I seemed ’pensive‘. She told me again how much she enjoyed the concert and that she was glad she was able to give me a ride home. Between classes, I rushed to the private toilet at the school library and had a little thrill when I removed my slacks and underthings to sit on the toilet.


Mimi picked me up just before noon. She was now wearing the flattering cerulean blue surplice wrap jersey dress beneath her black wool coat, finishing her ensemble with dark blue stockings and shiny black leather court pumps.

"Are you ready to go home and change into a dress, Evelyn?" she asked with a smile as we pulled away from the parking lot.

"Yes Mimi, I am" I replied softly.

"I picked some things out for you to wear. I enjoyed doing it. We‘ll have lunch when we get home; then you can go to your room and do your dressing, alright?"

"Yes Mimi, thank you." I was getting all creamy and was glad I was wearing a pantie napkin.


As we ate lunch, Mimi asked how everything went at school.

"There were no problems, Mimi" I had to admit.

As soon as lunch was finished, Mimi said with a smile and a wink: "Now up to your room, Evelyn, and out of those schoolboy clothes and into something appropriate for a fine young lady."

The dressing screen was adorned with the oh-so-pretty chiffon two-piece; pink and red roses and lilac against an ivory background. The matching scarf was casually draped over the screen. On the floor beneath the dress was a pair of white stiletto heeled T-strap sandals, taken from my mother‘s closet. Hung from the back of the screen was the white crepe de chine chemise and dance pantie, so beautiful with their profuse point de gaze lace with flecks of pink and blue in the lace. The matching foundations — brassiere, garter belt, and high-cut brief — were laid on the ottoman along with white silk stockings and the pair of delightful silk and lace tulip panties in white. The robe that matched the set was draped on the loveseat.

I had a lovely time dressing and arrived back downstairs a little over an hour later, walking unsteadily on the high heels. I had added the pearls and the pink chiffon hair bow just at the nape of my neck, gathering together my curled tresses. I was a fine young lady dressed for in the garden.

"So lovely, Miss Evelyn" said Mimi as she watched me as I descended the stairs. "Now you go sit in the study and do your homework. I‘ll bring you your tea."


I sat in the overstuffed leather chair in the study and cracked open a textbook, forcing myself to read. Mimi arrived a few minutes later with a pot of tea and the vitamins I had forgotten to take with lunch. A half hour later, the phone rang. Mimi answered and was soon in the study, carrying the portable phone.

"It‘s your mommy, Evelyn" she said, handing me the phone then leaving the room.


Our conversation didn‘t last too long, mainly because my stepfather was in the room and she couldn‘t talk. She did say that she had talked to Mimi earlier in the day, saying "…and Mimi says everything is fine. You can ask her later."

After the usual chat about sites, jet-lag, and itineraries, we hung up.

"I told her that you got her note and that you had asked for me to help you" said Mimi a few minutes later. "I told her what happened yesterday and that you would be dressing-up after school. Too bad your stepfather was in the room; I‘m sure your mommy would love to have a private conversation."


A few minutes later, she arrived back in the study with her camera, an older Nikon with a flash attachment — she hadn‘t yet gone digital. She was a good photographer and we had a couple of her photographs in the house. She had me pose in the chair holding my schoolbook, saying she wanted a couple of pictures of me as "a studious young lady".


Soon it was time for dinner and Mimi told me to go upstairs and freshen up. I spent several minutes at the vanity primping and freshening my makeup, thinking about my mother and what our ’private‘ conversation would be like.

I set the table and again had wine with dinner. Donning an apron, I cleared the dishes while Mimi went upstairs to my room. Soon, it was time for my nighttime routine. Mimi had chosen the moonglow sand washed silk set. On the ottoman was a fresh pair of the terrycloth panties and the same blue nylon and plastic briefs I had worn the evening before, as well as the white stockings. She had also laid out the white satin bustier.

It was much the same as the evening before; Mimi came up as I was sitting at the vanity in my bathrobe, just as I was finishing applying my overnight lotion. She was wearing her dark blue checked jersey robe and monitored me to ensure that I donned the couche-culottes. She had laid out the bustier, she said, not only because it had suspenders for my stockings, but also because it would protect the silk of my bed set. I liked wearing it because the padded breast cups gave me some shape. I found that I didn‘t need the shoulder straps and removed them. I brushed my hair out — one hundred strokes — and Mimi did a dozen or so strokes herself.

After she said her goodnights, I had a splendid time, my thoughts absorbed with the startling turn of events, the realization that I would be dressing every day, day in and day out until my mother and stepfather returned. And when my stepfather was gone, I would be dressing then as well.


Tuesday

Tuesday morning, Mimi again had me go to the bathroom, remove the terrycloth panties, and again show her that they were dry. The calves of my legs were sore — I guessed it was from wearing heels all the previous evening.

Mimi selected the blue silk surah foundations, chemise, and tap pantie for me to wear beneath my school clothes; soft stone-washed denim jeans, gray merino wool cable-knit sweater, and my hooded sweatshirt. I was a little less on edge at school and realized that Mimi‘s plan to make me more ’at-ease‘ might actually be working. She picked me up at the usual time, wearing her blue pleated skirt, black cashmere twin-set, shiny black leather court pumps, and a pretty scarf. "What time do you have to be at the library?" she asked on the way home.

"Not for an hour or so" I replied, adding that it was really up to me what time I arrived.

"Oh good, that will give you plenty of time to change."


After lunch, I entered my boudoir. Hung on the dressing screen was the pair of menswear-styled fawn colored rayon slacks and the matching fine silk and cashmere jewel neck sweater with off-white trim at the neck, waist, and cuffs; the very set that I had worn for dinner with Mimi and mother. On the floor was the pair of ecru-colored oxfords. Behind the dressing screen was my white silk charmeuse daywear and foundations, the shaping pantie, and a pair of white silk stockings. On the bed, Mimi had laid the new sweater jacket that mother had left for me in the closet; off-white with a shawl collar and hood and a self-tie belt.

Mimi knocked and entered, then walked over to the dressing screen and removed the slacks and sweater, holding them up and saying "I thought you should wear these things to the library today, dear."

"But Mimi, the slacks and sweater are just… just…" I stammered.

She completed my thoughts for me: "Too ladylike to wear? Nonsense" she replied. "If you wear that nice sweater jacket" she said, nodding at the bed, "no one will notice. Besides, you‘ve told me that you hardly see anyone but Melanie when you‘re at the library. And your mommy told me she thought you should dress nicely when you went to work, mentioning this sweater and slacks."

I sat down on the slipper chair and let out a little huff, saying "Oh Mimi —it‘s just all so… you know… so sudden."

"Now, now, Evelyn; you have to trust me, dear. I‘m doing this for your own good, so that when your mommy comes home, she won‘t have to deal with you droning on about not being ready to step out as her daughter."

"Yes, I know" I replied softly, bowing my head.

"Good!" she said with a smile. "Now get yourself dressed. I‘d like for you to wear those other earrings, too, and I think you should put your hair back with that nice barrette" she added, motioning to the vanity where she had placed my small gold hoop earrings and a thin gold hair barrette.

"Alright" I whispered, bowing my head again and looking at my manicured fingernails.

"Good. No more arguing, then? Now you go ahead and get dressed. I‘ll come up and check on you in half an hour."


I finished dressing and checked myself in the mirror — definitely too feminine. I turned to look at my derriá¨re — the shaping pantie really accented it. Fortunately, the sweater was roomy and the brassiere wasn‘t padded, so there were no telltale bumps. Then I donned the sweater jacket — it hid the sweater and my shaped derriá¨re, and the jacket itself was just androgynous enough that it wasn‘t immediately obvious I was entirely dressed in ladies things.

Mimi came to check on me and opined "You look very nice, Evelyn. With the jacket, it‘s hard to tell you‘re wearing ladies things." She was carrying a small tweed duffle bag with a shoulder strap that was part of mother‘s luggage collection. She put the duffle on the loveseat then went to my closet and retrieved the chiffon skirt I had worn the day before, along with its matching scarf. She held the skirt up to me and said "This skirt goes very nice with that sweater, don‘t you think?" I had to agree — the colors went well together, and the combination of chiffon and cashmere was quite fetching.

Mimi cleared her throat, saying "I was thinking, Evelyn, that it would be good for you to dress up while at work… another opportunity for you to become more comfortable. From what you‘ve told me, you have ample time alone. So I think you should bring this skirt along and change into it once you‘re upstairs. If, by chance, you have visitors, you can slip into the bathroom and change back to your slacks in a jiffy. It‘s just a thought, Evelyn; you don‘t have to dress up at work if you don‘t feel safe. But I‘d like for you to take these with you just in case you do decide that you want to be a lady librarian for the day."

She carefully folded the skirt and scarf put them in the duffle bag. "You‘ll need some other things, too. Fetch those sachets you use for padding, dear, and I want you to gather up some makeup and put it in this" she said, holding up a cosmetic bag that she had taken out of the duffle bag. She retrieved my pink and cream two-toned pumps from the closet, wrapped them in some tissue paper from the closet, and then put them in the duffel.

I couldn‘t argue with her — she wasn‘t making me wear these things to work, she was only suggesting that I might change into them if I felt safe. So I went to my drawer and handed her my sachets, blushing deeply, then sat at the vanity and selected a tube of lipstick, a compact of face powder, highlight blush and brush, a tube of mascara, and eyeshadow.

"Anything else you think you might need, Evelyn?" she asked as I handed her the cosmetic bag.

"Well… maybe" I offered, adding a hair brush, the bun curler and bobby pins. A proper librarian would put up her hair, I thought.


We arrived at the library a few minutes before two o‘clock. Mimi wanted to come inside and say hello to Melanie. I was able to put the duffle out of site on the stairwell before we greeted Melanie. She was pleased to see Mimi and offered us some coffee, leading us to her office.

We served ourselves coffee and then Mimi and I sat down on her office couch. Melanie sat opposite us in an overstuffed chair. I tucked my legs beneath me, trying to hide the oxfords with their cute Cuban heels. Melanie gave me a look-over and said "That‘s a very nice jacket you‘re wearing, dear. As are those slacks."

"Yes, they are quite nice" offered Mimi. "Ellen bought it for him. She wants Evel…" she paused for a moment, catching herself about to say ’Evelyn‘, then continued. "…Dahl… to dress up nicely for work and bought him this to wear."

"Yes, I can see that" she replied with a wry smile. "You look very nice in your sweaters, dear" she added, smiling at me.

She told us that she wanted to close early, around four-thirty, and asked if I could lock up when I left. "Sure" I replied. I wanted to get out of sight as quickly as possible, so I rose and took my coffee over to the cart that held a small pile of books to shelve, and then headed to the elevator with the cart, grabbing the duffle bag on the way. Mimi said she‘d come see me before she left.

Again, I had the upper floors to myself. I was shelving books when Mimi arrived.

"I have a few errands to run, Evelyn, and I‘ll pick you up around five-thirty. You know, that means you‘ll have an hour to yourself after Melanie leaves. It‘ll be dark by then. I think you should be dressed-up when I come to pick you up."

I started to protest; I was worried about being seen. Mimi reassured me, saying she‘d park close to the back door so I wouldn‘t be seen leaving the library and we‘d go right home using less traveled streets. She went through her reasons again; this little escapade would make me more comfortable and so forth. I gave in without further protest.


A bit after Mimi left, Melanie called me on the intercom and asked me to come downstairs to help her with something. Nervously, I made my way down the stairs.

Melanie needed me to retrieve some books from a tall shelf. "I could probably reach them" she said, "but my shoulder has been acting up. Can you be a dear and fetch them for me?" She had positioned a stool beneath the shelf. The task would require me to stretch a bit, which would fully expose the heels of the oxfords. I couldn‘t refuse her, and hoped that she‘d leave so she wouldn‘t see them, but she stood next to me, ready to receive the books as I retrieved them from the shelf. So I climbed the stool and stretched out for the books, exposing not only the heels of my cute oxfords, but the white stockings as well, although she had no way of knowing they were stockings rather than standard (albeit thin silk) ankle socks.

After I handed her the first set of books, she asked "Don‘t you want to take off your jacket? You must be warm, dear."

"No… I‘m okay" I replied.

"Are you sure?"

"Uh-huh" I replied, reaching for the next set of books. As I handed her the books, the belt around the jacket slipped and the waist of the jacket bunched up around the misplaced belt.

"Dear, you‘re going to stretch that sweater all out. You really need to take it off" she said empathically. She was right, off course, and it was awfully hot with it on. So I stepped off the stool and removed the jacket, draping it over a chair and then straightening the pullover sweater.

"What a cute sweater" she said as I returned to the stool.

As soon as I stretched for the next set of books, I really regretted taking off the jacket, for the sweater pulled up in the back and I was sure that my silk charmeuse camisole revealed itself. I wondered if the outline of my brassiere clasps were showing beneath the sweater as I stretched. If they did, Melanie didn‘t say anything.

I had one more set of books to fetch and then I was done. I hurriedly slipped back into the sweater jacket. I was able to escape a few minutes later, my heels clicking on the hardwood floor as I made my way to the stairs, aware that Melanie was watching me.


A half-hour before Melanie left, I began to transform myself into the coy young lady librarian that I fancied myself. I minced about in my chiffon skirt, my heels clicking on the hardwood floor, my hair done up in a bun, my face tastefully made up; the demure and diffident librarian tending to her books. Catching glimpses of myself in the few mirrors, I soon became rather aroused. I was being so naughty.

I was nervously waiting by the back door form Mimi to come and pick me up. I was so nervous, my palms sweaty. I was stepping out again, just like I had with Auntie. I kept telling myself that it would be alright, that I wouldn‘t be discovered, that I would be safe and secure driving the short distance back home with Mimi. She finally arrived and I dashed out to her car. She giggled at my furtiveness, saying I raised more suspicions by acting so nervous. We drove home without incident. It was but a brief stepping-out, but it was still oh-so-thrilling.

After we arrived home, I went to my room and touched up my makeup and added a bit more jewelry. As I sat at my vanity, I thought about Melanie and how she must have known I was all crossdressed, and how my holiday was turning out so much different than I had anticipated.

My original plan — before Mimi had taken charge — was to stay home on Wednesday and Thursday, giving myself five whole days to indulge in my desires in private. But now that Mimi was staying at the house with me, I had been reconsidering. Mimi worked at the art gallery on Thursdays, so I definitely wanted to stay home then and have a very private day. But my little escapade at the library had left me in such a mood, so I decided to go through with my plan. After dinner, I told Mimi that I thought I was getting a sore throat and there might be a possibility that I wouldn‘t be attending school the next day. I sweetened the ruse by saying that I was all caught up on homework and I just had some easy reading to do.

Mimi‘s reaction was more than I expected or wanted. She put her hand on my forehead to feel if I had a fever. She took my temperature, which was slightly elevated (for no reason, actually). I guess I looked the part as well, for the emotional events of the last few days had left me tired. She readily agreed that I should stay home the next day and had me take various vitamins. She suggested that I go take a nice warm bath and even went upstairs and drew a bath for me, adding bath salts and bubble soaps.

While I was bathing, she laid out a bedtime dressing of my blue surah silk chemise, tap pantie, and the white bustier, along with the white cotton stockings I had been wearing and the couche-culottes with the baby blue plastic pantie briefs. Dressed in my thick terry bathrobe, I applied my overnight lotions, donned the things she had laid out, and brushed out my hair. She checked on me, ensuring that I was wearing the couche-culottes and had applied lotion, and then tucked me into bed. Of course I didn‘t fall asleep right away; there was a lovely long and gentle creaming to attend to.


Wednesday

Mimi knocked on my door at the usual time, interrupting the beginnings of what promised to be a lovely time with my pillows. I untangled myself, called out "just a minute", threw on the robe, and unlocked the door, trying to hide my aroused state. I quickly returned to bed, sitting up and covering myself. She was wearing her blue robe and black ballet dress as a nightgown. She came in and sat on the bed next to me.

"How are you feeling today, dear?"

"I feel okay, Mimi" I replied, trying to sound a little under the weather.

"Do you feel well enough to go to school?" she asked.

"I suppose I could, but I‘d rather stay home" I replied.

"No problem, dear. Just stay home today and take care of yourself."

"I think I should" I replied.

"Now, Evelyn, I have to ask: did you wet yourself last night?"

"No, Mimi" I whined.

"Just checking, dear; it‘s alright if you did. I would have found out anyway."


I came down for breakfast. It was a raw and blustery fall day and Mimi had already lit a fire. As we were eating breakfast, Mimi said "Since you‘re staying home today and taking it easy, I‘ve got an idea. Why don‘t we both dress up in something really nice? You could dress-up in that pink chiffon dress your mommy bought for you — I‘d really like to see you in that dress. And I‘ll dress in my blue chiffon evening gown. Then we‘ll take some pictures — I‘d like it if you could take a few of me. We can both start with a nice bath. How does that sound?"

"That sounds like fun, Mimi" I replied. How could I refuse?

"I‘d like to go to your mommy‘s room and take a bath, if you think that would be alright."

"Of course it would, Mimi — you don‘t need my permission" I said earnestly.

"Do you think it would be alright if I wore some of your mommy‘s jewelry?"

"But of course, Mimi! You know… she left her diamonds behind… They‘d look so pretty against the blue chiffon" I suggested.

"What a wonderful suggestion, Evelyn. Thank you."


She went to her room and retrieved her blue evening gown and asked me to take it upstairs for her. She‘d be along in a few minutes. I was happy to lay it out on mother‘s bed; after all, Mimi was setting out things for me to wear. I took out my mother‘s diamonds and put them next to Mimi‘s dress, opening the presentation boxes for her. I even brought out mother‘s diamond tiara.


As I went to my boudoir to begin my bath, I met Mimi in the hallway. She was carrying a laundry basket and a canvas bag. The canvas bag contained toiletries and things for her bath. I couldn‘t help but notice what was in the laundry basket — underneath a pair of blue pumps was a mound underthings — black lace over white satin. I couldn‘t tell what the exact items were, but thought to myself ’oh my‘ as I headed to my boudoir, realizing that Mimi would be wearing such racy underthings. In one sense, it made me queasy — wearing such unmentionables. On the other hand, it was comforting to know that she really meant to dress up, as I did.

I bathed, thinking about Mimi and her lingerie. After powdering and doing my nails, and before dressing in the pink satin foundations and the lovely pink daywear mother had bought me, I partook of a bit of hashish, figuring that Mimi wouldn‘t notice by the time we both finished dressing. While romantic classical music filled my bedchamber, I really got into my dressing, donning the foundations, adding a lace-trimmed damask handkerchief pantie napkin, a pair of tulip panties over the bikini panties, slowly drawing on pink silk stockings, and then finishing with the daywear; camisole, dance pantie, and pettislip. I slipped into the white crepe de chine long robe with its bell sleeves and lace-adorned shoulders and sat at my vanity to do my hair and makeup. I went fairly dramatic with my makeup, really bringing out my eyelashes with mascara, doing my eyeshadow hues of pink and lilac transitioning to a deep plum, adding a bit of shadow beneath my eyes, just like my makeup book said I should do. My cheeks glowed softly with pink blush, my lips all pouty in plum. My hair was curled and gently drawn back into the pink chiffon hair bow, exposing the pearl-drop earrings. I was having a delightful time, suspended in a sort of limbo state, all creamy and dreamy.


With serendipitous timing, there came a gentle knock on the door. "Evelyn dear? Would you be able to help me with my dress?" Mimi asked from the other side of the door.

"Of course, Mimi" I replied, closing my robe around me and opening the door. She was wearing her blue robe. She had done her makeup and looked fabulous. "Wow!" I said, unable to restrain myself "you look so pretty!"

"Why thank you Evelyn. But not as pretty as you" she replied with a wink.

I followed her to mother‘s room. The blue evening gown was still on mother‘s bed where I had laid it. It suddenly dawned on me what was going to happen next; Mimi undid the sash to her robe and removed it, revealing her set of white satin foundations overlaid with black lace; a long line brassiere, a waist cincher with suspenders, and a pair of briefs, along with black stockings with lace tops. Even though Mimi was older and matronly, she still had a great body and skin; nothing old or wrinkled like I expected. I realized that my perception of women in their forties was totally wrong — they weren‘t wrinkled old hags! That and the fact that she was wearing such a risqué set made me blush beet red.

"Ah, Evelyn… now don‘t disappoint me and think that just because I‘m older doesn‘t mean I can‘t wear nice underthings like you" she said with a smile.

She took the dress from the bed and stepped into it. I stood behind her and guided her arms into the sleeves and brought the dress around her shoulders. The zipper in the back was long and prone to snagging, and I could see how she would have trouble with it. I took my time, both to ensure that the zipper didn‘t catch and because it seemed like the right thing to do. After I zipped her up, she sat at my mother‘s vanity and asked me to fasten the diamond necklace. I could sense that the nape of her neck was sensitive to my touch, so I was as gentle as possible, barely touching her nape as she bowed her head and I helped her gather her hair. She gave a quiet little ’hmmm‘ as I took the necklace and carefully clasped it. The air became heavy with sensual tones and I had to quell my feelings; after all, this was Mimi — she was almost family.

"Would it be alright if I brushed your hair, Mimi?" I asked softly. Her hair did need a brushing, and I wanted to reciprocate for when she brushed my hair.

"How sweet of you, Evelyn; yes, please do."

I spent a good ten minutes brushing her hair. She seemed to really enjoy it, letting quiet umm‘s and ahh‘s escape occasionally. I complimented her a few times, telling her how beautiful she looked. Then I helped her with the tiara. We both decided that it didn‘t really work, so I put it back in its presentation box. She had done most of her makeup already, but after I finished brushing her hair, she put on some finishing touches as I stood behind her. I helped her into the diamond bracelet. I then offered to help her with her black pumps, bending down and kneeling on the floor.

"Oh my, Evelyn" she whispered as I guided her stocking‘d feet into the pumps. "I never would have thought that such a fine young lady would be attending to me like this."

"My pleasure, milady" I replied with a smile. We both giggled. "Really — I‘m happy to help you Mimi. You‘ve been so kind to me" I added.

She rose and took a few turns in the dressing mirror. I complimented her again. "Well, let‘s get you finished, Evelyn" she said with a wink.


Back in my boudoir, she helped me dress in the same way that I helped her. She had me stand in front of the cheval mirror and held my lovely petal pink chiffon dress open for me to step into. Then she guided it up, arranging my pettislip as she did, and slowly zipped me up as I watched my reflection. When she was done, she had me do a turn and said "Oh, you are so pretty in your pretty dress. You are so lucky to have such a lovely dress. I‘d have loved to have a dress like that when I was young." She had me sit at my vanity and helped me with my pearl necklace and bracelet, then sat on the loveseat as I raised my legs for her to slip on my pink heels.

We proceeded downstairs. Mimi had brought a camera tripod to hold the camera steady for the low indoor light. Mimi struck some elegant poses by the piano and I clicked away. Then I had the idea of bringing out some of mothers furs; the white fox capelet and the natural mink coat trimmed with sable. She posed with capelet, but not the coat since it was too small for her. Then it was my turn. Mimi guided me through a few poses by the piano and a few by the fireplace.


We had a light lunch with a glass of wine and my usual vitamins. Afterwards, Mimi suggested that perhaps I should take an afternoon nap. "After all, dear, you‘re still under-the-weather and we just can‘t let you become sick. Let me attend to your room and put out some things for your nap."

"Okay, Mimi, that sounds like a good idea" I replied. I certainly didn‘t need any encouragement — I was in a really creamy mood and nothing would suit me more than to have a lovely afternoon nap.

"In the meantime, why don‘t you fix us a pot of tea and bring it upstairs? I brought some of my favorite tea — you‘ll find it on the counter. It‘s a nice relaxing tea, good for helping you sleep. You should mix it with your special tea that your mommy wants you to drink — half and half should be about right."

I went to make tea, finding Mimi‘s tea in an unlabeled tin. As she had suggested, I mixed it half and half with my tea and put it into the infuser. After adding the boiling water, I put a tea cozy over the pot, and set it out on a silver tray with two cups and a little bowl of honey, then gingerly made my way upstairs. I was almost titching by the time I reached my room. Mimi was sitting in one of the wingback chairs, her legs crossed. She had me put the tray on the table between the two chairs. After I set the tray down, she rose and guided me over to the cheval mirror and wordlessly unzipped my dress and had me step out of it, holding my hand to steady me for I had neglected to remove my heels. She placed the dress on its padded and scented hanger and hung it from the dressing screen.

"Now go and change into the things I‘ve laid out for you dear. I‘ll be back in a few minutes. There‘s something I want to discuss with you."

I went behind the dressing screen, wondering what lovelies she had chosen for me to wear for my nap. I was surprised to find things from the dove gray with peach trim soft combed cotton set mother had bought me; the camisole, culottes, and robe. On the ottoman were the couche-culottes; terrycloth panties and the pink nylon and plastic panties. Although Mimi was making me wear the couche-culottes at night, I was a little surprised to see them laid out for an afternoon nap.


I first took the opportunity to use the toilet, for the wine had its usual effect on me. Mimi arrived about the time I had finished changing. My foundations and daywear were scattered about the ottoman or draped over the dressing screen. I drew the robe around me, slipped into the pair of white satin stiletto-heeled boudoir slippers and stepped out to find Mimi sitting in the wingback chair, pouring me a cup of tea. On the floor next to her was a laundry basket containing Mimi‘s blue robe and what looked like a folded small green flannel sheet — I recognized it as the waterproof bed liner that mother had put on my mattress when I was so sick with hepatitis.

"Come sit, dear, and have a cup of tea."

I took a few sips — it didn‘t taste much different — and put the cup down. "Drink it all, dear." As soon as I was finished, she poured me another cup. She had hardly touched hers. What was going on? I thought.

"Evelyn?" she began, clearing her throat and turning a bit to face me better, crossing her legs again and then straightening out her skirt "I want you to drink a lot of tea — several cups."

"What? Why?" I asked.

"Well, for my peace of mind, and yours perhaps, I want you to, um, test the couche-culottes to see how much of your water they can hold."

"What? Eww…" I whined "You mean you want me to, you know… pee?"

"Evelyn, please don‘t use that sort of foul language. If you must, say ’pass water‘ instead."

"Eww…" I said again, meaning for it to come out as an expression of disgust, but it came out differently; more of an expression of pleasurable anticipation. Three thoughts raced through my mind. First was how dare she violate my privacy by asking me to wet myself. Second was that I would have to protest for my own dignity. Third was how thrilling it would be to ’test‘ the couche-culottes, to feel what it was like to wet myself. I tried to think of something to say, but just sat there stunned, my mouth open. Finally, all I could do was to let out a soft whine of "Mimi…" and bow my head.

"Now, now, Evelyn; you‘ll be fine" she said in a reassuring tone. "It‘s something that must be done, something I need you to do for my own peace of mind. The last thing we need is for you to have an accident one night and wake up to find your lovely bedthings all wet. Don‘t worry… you‘ll be fine, dear. So while you to drink your tea let me explain some precautions I‘ve taken. I chose those cotton things for you to wear so that if there is any leakage, we‘ll be able to see the wetness on the cotton and not on one of your lovely silk panties. Also…" she paused, reaching into the laundry basket by her chair and removing the waterproof bed liner "…just in case they don‘t hold, I want you to lay down on top of this while you‘re napping to protect your nice sheets."

"But… but" I stammered. I just didn‘t know what to say.

She sat back down, crossed her legs again and said "Don‘t be so negative, Evelyn. It‘s not like I‘m asking you to do something horrible. It‘s just a little test. Now drink your tea. I‘m not leaving until you drink most of the pot."

What little shred of dignity I had left disappeared. If Mimi‘s intent was to make me even more submissive to her will, she had succeeded; I couldn‘t mount a protest because I wanted to know what it would be like — it was so naughty and taboo and forbidden, such an acquiescence of control. In a way, I found it erotic. The response I made summed up all my emotions…

"Yes, Mimi."

"Oh good, Evelyn; I‘m so glad you‘re not putting up a fuss. You‘re such a sweet young lady, you know that?"

"Thank you, Mimi" I replied as I downed the cup. The discussion seemed over, and she poured me another cup of tea, then rose and went behind the dressing screen, gathering my foundations, and putting them in the laundry basket. Much to my embarrassment, I had left the lace-trimmed damask handkerchief in my panties and they fell out when she put the panties into the laundry basket. She picked up the handkerchief, gave a little ’hmm‘ of comprehension, and put it in the laundry basket. We chatted about the photography session we had that morning and how much fun it was. Quite suddenly, I had an almost uncontrollable urge to go. I wondered if the tea Mimi had me mix with mine was making me need to go. I suspected that it was.


"Mimi?" I interrupted, my voice soft and lilting, "I… I have to go."

"You mean you have to pass water? Alright dear, it‘s alright. Now you may find this difficult at first. Here‘s what I suggest you do. Go into the bathroom and stand or sit as you would normally… subconsciously, your body will then naturally relax. I‘ll wait here."

I stood, placing the palms of my hands on the front of my hips, my head bowed as if observing my couche-culottes, my long hair falling in front of me. "Okay, Mimi, I guess that makes sense…" I lisped.

I went to the bathroom, closed the door and stood facing the mirror above the sink. I really had to go, but, as Mimi had warned, my subconscious was preventing me — it was demanding that I remove my clothing as I normally would. It was a bit of cognitive dissonance — I had to concentrate on relaxing. Watching myself in the mirror, I slowly opened my robe. I wasn‘t yet to the stage of bursting, but I was close. I put my hands on the sink and bent over slightly, my breathing shallow. My whole body tingled in anticipation of relief. I felt flush, a little clammy. Then I felt a shivering chill move from my shoulders to my toes — what a sensation! My entire being was aware, tingling; it was not unlike some of the sensations I felt just before an orgasm. With an audible gasp, I trembled and shuddered and my water began to flow in a steady but weak stream — hardly a normal release. I had to will myself to increase the flow, sending another shiver down my spine. At first, I couldn‘t detect anything, but then I could feel the moisture spreading over the thick terrycloth panties and then… I could feel my water trickling down the sensitive skin around my daintie and I had an involuntary contraction, stopping my release. It hurt and I let out barely audible gasp. I had to begin again, for my bladder was crying for release. Again I concentrated, my breathing quick and shallow, and my body tingled and shivered and shook as the moment of relief arrived and I began to pass water again. Then another chilling shiver went down my spine. My subconscious finally acquiesced to the unfamiliar situation and I was able to let more water flow. I could not only feel the trickle on my skin, but could feel the pad begin to absorb my water and expand. Everything was becoming warm and moist beneath the protective panties. I was able to straighten up and watch myself in the mirror as blessed relief washed over me; my body had relaxed and I was now wetting myself with a steady but still somewhat weak stream. A minute or two had already passed, yet I felt that it could maintain the wetting for several more minutes. The chill was fading, replacing with a warm, almost cozy feeling. I looked at reflection and fondled my hair and let out a quiet moan of ’oh my…" Now I was very aware of how moist and warm the terrycloth panties and the pad between my legs were becoming. It didn‘t seem too bad; I squeezed my legs together and could tell that the pad still had capacity to absorb my water. There was no leakage. My stream faded to a meager trickle — I had relieved myself enough that I could have contracted and stopped the flow, but it seemed effortless just to stay in my current relaxed and subdued limbo state and let the trickle continue. The only one of my senses that wasn‘t affected was smell; I couldn‘t detect any. Perhaps it was the chamomile or something else in the tea, or the plastic panties working as they should.

I stood fondling my robe and hair, amazed at what had transpired and the state I was now in. The sensations that I had experienced were like nothing I had ever experienced before — the ache of fullness giving way to chills and tingles, how flush and fluttering I felt, how I quivered and shuddered and everything became tranquil and still as my water began to flow, its moist warmth spreading beneath my panties. It wasn‘t as intense as a creaming, of course, but the sensations were still intensely pleasurable. And through it all, I had remained stock-still; my entire being totally consumed with a simple biological act. The physical sensations I had just experienced, and continued to experience, had emotional counterparts as well, for here I was dressed and made up as a girl, wetting myself. It was a shameful; I was such a sissy.

I knew that this would not be the last time; oh, far from it. Mimi had done this to me. She had introduced me to this new source of pleasure. She must have known how it would affect me; I was completely enthralled.


My reverie was broken by Mimi asking "Is everything alright, dear?" Her voice was gentle and empathetic.

"Yes, Mimi; I‘m alright" I replied softly.

"Have you passed water yet, dear?"

"Yes" I lisped.

"Then you should come on out, dear, and let me see."

I opened the door, leaving my robe open, and gingerly walked into my boudoir, almost mincing on my heeled boudoir slippers. She reached up and stroked my hair, asking "That wasn‘t so bad, was it dear?"

"No… It was… it was okay" I replied in a high sing-song voice.

She opened my robe to expose the cotton culottes and had me turn for her — she was looking for signs of wetness on the gray cotton culottes. "Oh good" she said upon seeing no wetness.

"Now dear, before you take your nap, could you help me out of this dress?" she asked nonchalantly.

"Of course, Mimi" I replied softly.

She sat on the loveseat and I helped her remove her heels. She then stood facing the cheval mirror and I stepped behind her and began to unzip her. I couldn‘t be sure, but it felt like I was passing more water as I finished with the zipper and helped her out of the dress. She stood in her black lace over white satin foundations, not moving, facing the mirror.

"What do you think, Evelyn? Do I look good in my lingerie?" she coyly asked, laying on a thick French accent, looking at my reflection in the mirror.

I blushed deep red. "Oh Mimi" I whispered.

"I‘ll take that as a yes" she said with a smile, and then retrieved her blue robe and slipped it on. Then she sat in the wingback chair, crossing her legs again, letting her robe open to reveal them.

"Come sit for a minute. I‘d like you to have another cup of tea."

Sitting down on my wet couche-culottes was quite an experience. For the first time, I really felt the fullness of the pad as it squished against me. I didn‘t dare cross my legs, but sat upright, my knees almost touching, my feet elevated by the stiletto heels of the marabou-trimmed boudoir slippers.

"Mimi — I… I don‘t think I should have anymore" I said hoarsely, just above a whisper. "It makes me have to pass water."

"I realize this dear. But as I said, this is a test. If your couche-culottes can hold four cups of tea, then they should definitely last overnight."

"Yes Mimi" I replied. I was beyond and point of disagreeing with her — she had completely subdued me and we both knew it.

She poured my tea and as I sipped, she told me that she wanted me to continue wetting your couche-culottes unless there was a flood of water escaping and wetting the bed.

When I finished the cup, she helped me take off my robe and had me lay on the bed on top of the waterproof bed liner. She then covered me with the chenille throw blanket, her robe opening as she did so. She bent down, kissed me on the forehead, reminded me again that we were testing my couche-culottes, and left the room, closing the door.


I lay in bed, still stunned by what Mimi had done to me, shocked by the new source of pleasure that she had introduced me to. I began to pass more water. I could feel it trickling over me beneath my lace accented plastic panties. Soon after I finished passing, my daintie became so very aroused. I rose from bed and went to the bathroom, carrying a pillow with me. I took off my cotton culottes — they were still dry. I took a bath towel and wrapped it around me to absorb any wetness that might escape when I placed the pillow between the countertop and my daintie and began to churn, my face close to the mirror, whispering my O‘s. My couche-culottes were so warm and squishy and it took just a minute or two to add my cream to the thick and wet terrycloth panties.


I put on the cotton culottes and managed to make it back to bed before I had to pass water again. I lay on the bed liner, wetting myself, the couche-culottes nearing capacity. Laying in my warm wet couche-culottes, I drifted off to asleep — I guess the tea did have a tranquilizing effect.


I woke when Mimi entered the room. She was carrying a white plastic trash bag, the kind that we used for the kitchen refuse bin. She was still dressed in her robe and foundations.

"Let‘s see how you did, Evelyn" she said brightly. She turned back the covers and inspected me.

"Tsk, tsk; you‘ve had a bit of leakage" she said. I looked down and saw a wet streak at the hems of the pantie legs. I was surprised there wasn‘t more.

I rose gingerly. She cautioned me to be careful not to sit on the bed and retrieved a bath towel and laid it across my path over the bed. Awkwardly, I made my way out of bed and stood as she continued her inspection.

"What do you think?" she asked me.

"Well, given how much water I had to pass, I‘m really surprised I‘m not completely soaked" I said softly. But as I stood there, the stain of wetness grew; gravity was causing leakage.

"Into the bathroom with you" said Mimi. I heard her open my bureau drawer behind me. She came into the bathroom carrying my robe, the plastic bag, and a fresh pair of terrycloth panties, without the pad. She opened the plastic bag and withdrew a pair of plastic gloves, the kind used in restaurants, as well as another plastic bag. I had no idea where she got the gloves. She told me to put them on, then remove my soiled couche-culottes and put them in the plastic bag, wash myself, then slip into the fresh terrycloth panties. She then left me alone. I donned the gloves and gingerly removed the soaking wet couche-culottes and put them into the plastic bag. I then washed my pelvis and legs with a washcloth and drew on the dry terrycloth panties — they felt really nice. I thought I‘d be able to smell the soaked terrycloth panties when I removed them, but there was only a faint odor, which was not unpleasant. I again suspected the tea had something to do with it.

A few minutes later, I came out of the bathroom. Mimi wanted to hold the plastic bag to feel its weight.

"Yes, I‘d say you did a thorough job of wetting yourself" she said with a giggle, hefting the plastic bag. Then she instructed me to put on the gloves again and remove the absorbent pad from its terrycloth cover and put it the other plastic bag, and then rinse everything else out. "Then we‘ll put them in the washing machine" she added at the end.

After completing these tasks, I donned the cotton pajama bottoms and together, Mimi and I went through my laundry hamper and lingerie drawers and selected things that needed washing. We left out my white crepe de chine things because Mimi thought I‘d need them that evening. I followed her downstairs to the laundry room and we put the couche-culottes into the washer. "You want these to be nice and soft next to your skin" she said as she added fabric softener to the wash. She then showed me how to hand wash my brassieres, garter belts, and stockings. We put these on the drying rack. All my other things could be placed in lingerie bags and machine washed on the gentlest setting. Mimi said she‘d take care of them once the couche-culottes had finished.


She then made a suggestion for the rest of the afternoon and evening; First, I should bathe and apply lots of lotion and powder to my pelvis and derriá¨re to prevent the possibility of a rash. Then she wanted to see me dressed in the midnight blue silk faille gown that mother had bought me long ago. We‘d have dinner and then she would show me how to properly iron my lingerie.

I had a couple of hours to bathe and dress. I donned white crepe de chine foundations, the delightful new silk and lace tulip panties from Auntie, the pair of high-cut white briefs, the crepe de chine chemise, and dance pantie, and new blue silk stockings. I slipped into the matching crepe de chine long robe and sat at vanity and did my hair in a fetching bun. I carried the blue of the silk faille skirt and the lapis to my eyeshadow and did my lips in a reddish purple. I felt lightheaded when I drew on the petticoat and then stepped into the gown. I finished the ensemble with mother‘s lapis and gold jewelry.

I came downstairs to find Mimi dressed in her long black rayon skirt with the self-tie sash, her white rayon lace band collar blouse, sans neck scarf, and her black pumps. She still had on her makeup from earlier in the day.


"The mail came dear — there are some pictures" she said, handing me the envelope. I knew immediately what they were — the pictures my mother had taken of me.

"Go ahead and open it dear — I know what they‘re the pictures you mommy took and I‘d like to see them" she said kindly. "Come, let‘s sit down together."

I really didn‘t want to share them with her, but she was more or less insisting. We sat and I opened the package. It was chilling to see the photographs — could that possibly be me? There I was, sitting so demurely on the couch, my knees together and my hands folded in my lap, looking ever so much like a wealthy and kept young lady in the St. John‘s knit. Then there were the poses by the piano and the dinner table.

Mimi stroked my hair as I went through the photographs. "See, darling? She how pretty you are? No wonder your mommy wants you to dress as a girl." I was stunned, my mouth hung open. I couldn‘t say a word. I couldn‘t believe how pretty I was, how much I looked like a girl and not like a boy dressed up as one. We went through the stack a couple of times, Mimi commenting on each one. Most of the photographs were bad — it was a cheap camera and the lighting wasn‘t great, but there was a really good one of me standing at the dinner table with the candelabra and chandelier behind me. Mimi said we simply had to put the photograph in a frame. She left the couch to find one — we had some empty frames in a cabinet. She found one and put the photograph in. "I want to put this in your mommy‘s room" she said, taking it away and up the stairs.


She had prepared a nice dinner and we ate in the formal dining room on our best china. She told me during dinner that she was thinking of getting a digital camera. We talked about the advantages and she noted that she liked the privacy of not having to send film to be developed. She suggested that maybe I could do some research on the latest and best cameras for her, and I readily agreed.

Then she had me iron my blue silk surah set and the brassieres and garter belts I had washed. She instructed me to iron them with a warm iron while the things were still a little damp, and turned inside out. I knew how to iron clothes, but she showed me a couple of tricks I didn‘t know. The other things that needed washing would wait until later so that they didn‘t dry completely before we had a chance to iron them.


When I had finished ironing, we both went upstairs carrying the laundry. Mimi had produced a container of baby powder from her room and brought it along. She helped me out of the bolero jacket and unzipped me, then had me finish undressing behind the dressing screen then slipping into my terrycloth robe. I went to the bathroom and began my nightly routine of removing my makeup and applying moisturizing lotion, paying particular attention to my pelvis and derriá¨re.

When I exited the bathroom, I saw that Mimi had brought one of the cream silk tuffets from mother‘s room and set it by the vanity chair. I went behind the dressing screen and found the freshly laundered blue silk surah robe, chemise, and tap panties waiting for me, along with the white satin bustier and white cotton stockings she had me wear at night. And, of course, the couche-culottes; white plastic pantie briefs this time. The container of baby powder was next to the couche-culottes. Mimi spoke from the other side of the dressing screen, telling me I should apply the baby powder to the inside of the terrycloth panties before putting them on, then applying more after I had drawn them on. "It really helps prevent rashes and other problems" she added.

After dressing, I sat at my vanity, my robe a little loose. Mimi sat behind me on the tuffet and brushed my hair. The tuffet was taller than my slipper chair and allowed Mimi to comfortably brush my hair. Sitting on the tuffet, she was a head taller than me and we could see each other easily in the vanity mirror.

"Did you have a nice day today, sweetheart?" she asked as she began to draw the brush slowly through my hair.

"Oh yes, Mimi; it was wonderful" I replied softly and truthfully.

"Oh good; I had a nice day too. It was fun for me to dress up in my eveningwear. And it gave me a chance to wear my, um, special underthings. I enjoyed it. And tell me… our little test of your couche-culottes went well, didn‘t it?"

"Uh huh."

"I‘m glad to know that if you wet yourself tonight, you won‘t sully the lovely things you‘re wearing, or wet the bed, either. Aren‘t you glad to know that, too, dear?"

"Yes, Mimi, I am glad" I lisped.

She finished brushing and pulled my hair back into a ponytail, using an elastic band. She turned down my bed before leaving, saying "I think I‘ll turn in myself and do a little reading…" adding, with a wink "I‘m in the middle of a really good ’bodice-ripper‘." With a kiss on my forehead, she left.


I sat at the vanity for several minutes in disbelief of the day and how Mimi, in one day, had completely wrapped me around her finger and subdued me, mostly by having me wet myself, but also with two delightful dressings.

I wasn‘t tired and I had lots of time to orchestrate a bedtime creaming. But I had a decision to make — I so wanted to experience again the pleasure I had that afternoon, but there was no way I could do so without Mimi knowing. But I just couldn‘t deny myself. There was only one recourse — go ahead with the experience and then tell Mimi in the morning that I had wet myself while sleeping, admitting that I was a bed wetter.

I went to the bathroom and drank a big glass of water (I wasn‘t worried about over-wetting myself; I could always use the toilet before the saturation point was reached). Then I took a bottle of my basic moisturizing lotion, opened the waist of my couche-culottes, and squeezed a good bit of the lotion all about my daintie. I turned on the fan and partook, elevating my senses. I turned on some soft romantic music and sat back down at the vanity. As the hashish rush came to me, I let down my hair and applied some lipstick, waiting for the glass of water I had drank to take effect, thinking about Mimi‘s cosseting of me and just how different my holiday was turning out to be than what I had planned. I practiced what I would say to Mimi the next morning.

I felt flush, tingling as my wetting neared. Sitting on the edge of my seat at my vanity and fondling the lace of my robe, the straps of my camisole, and my long hair, I gasped "Oh Evelyn" and began to pass water, reveling in the same sensations I had felt that afternoon. But unlike that afternoon, my couche-culottes easily held my water. Now warm and moist, I dove into a long, slow, luscious pillow-ride. I tried to keep my cries and yips of pleasure quiet, not wanting Mimi to hear me as she read her ’bodice-ripper‘. The house was still and quiet — even though I had music softly playing, she might hear my louder cries if she was listening. The toe-tingler arrived and I creamed in my warm moist couche-culottes.

I lay in bed, deeply satisfied, and wetted myself again. I had a blissful sleep full of dreams of lace and angora.


Thursday

I awoke early and used the toilet, but drew the moist couche-culottes back on, then went back to sleep and woke when Mimi entered an hour or so later. Today was her day to work at the art gallery, and she was dressed for work in her blue pleated skirt and black twinset.

After our greetings, I sat up in bed. I had been practicing for the moment. Fingering the shoulder strap of my chemise, my head bowed, I said with a soft lisp "Mimi? I… I think I wet myself last night."

"Oh, Evelyn…" she said in a concerned voice. She sat next to me on the bed and gently stroked my back and in a soft reassuring tone, said "It‘s alright Evelyn. I thought it would happen. Once your subconscious realized that you could safely wet your couche-culottes and not your bed and things, it let go. Don‘t be disappointed, dear. Being a bed-wetter is just something you‘ll have to accept and deal with."

Of course I wasn‘t really a bed-wetter; I had consciously wet myself. But I couldn‘t tell her that; I just let her think that I was. I didn‘t know how to respond.

"Are your panties wet?" she asked, rubbing my back gently.

"I don‘t think so."

"We should look." I was sitting up, my legs folded beneath me, the bedcover draped over my legs and hiding my panties. Mimi removed the bed covers and instructed me to sit up on my knees and lift the hem of the chemise. She looked behind me first, saying "Your panties look dry, dear… let me check." I didn‘t expect her to do what she did — she felt my stocking suspenders and fingered the fabric at the bottom hems of my panties. "No… you‘re dry back here" she declared softly. Then she repositioned herself to look at the front of my panties and again felt the stocking suspenders and my panties. "It seems that the couche-culottes held your water, Evelyn" was her conclusion.

I sat back down and folded my legs and she pulled the bed covers back over my legs. She began to gently rub my back again and after a few moments, she said in a near whisper: "Now don‘t be too harsh on yourself dear. You‘re very delicate and frail, you know, and bedwetting is to be expected. It‘s alright; it just means you‘ll have to wear couche-culottes at bedtime."

"Yes, Mimi" I said, trying to sound a little tearful, blinking my eyes so that they moistened.

"There, there, sweetheart; I know you‘re feeling ashamed right now… and, how shall I say it? …inadequate."

Her words stung me a bit. Yes, I should feel ashamed, I thought. I was inadequate. I bit my lower lip and sniffed back my tears, and nodded my head slightly, whispering "uh-huh."

"Oh, you poor thing you… I‘m sorry. I shouldn‘t have said that. You‘ve got so many emotional issues you‘re dealing with, dear… I shouldn‘t be adding more. But I do think that dressing up in ladies things helps you to alleviate your feelings of shame and inadequacy doesn‘t it? Those feelings disappear when you dress up as a pretty young lady, don‘t they?"

"Yesss…" I lisped in reply. Her meaning was clear to me — I was an insufficient and inadequate boy, much more suited to being a young lady.

"So that‘s just what we‘ll do, dear; keep you dressed as a fine young lady… and make sure you wear your couche-culottes at bedtime, right?" she asked softly.

"Yes, Mimi" I sniffed. A moment later, I added: "Thank you, Mimi."


"Now…" she said cheerfully, sitting upright, "…are you too wet to help me change the sheets on your bed? Or do you need to change now? Because I‘d like to do that before I leave. Then you can go downstairs and take care of your wet things, just like we did yesterday."

"I‘m okay, Mimi. I‘m not very wet. " I replied.

Together we changed the sheets and pillowcases, removing the petal pink satin bed linens and dressing the bed in the fine Egyptian cotton sheets and pillowcases. Mimi fluffed and arranged all the pillows, leaving the heart shaped boudoir pillow for last.


I followed her downstairs carrying the bed linens and a dry pair of terrycloth panties. Looking outside, I could see it was again a raw and blustery day; a day to stay warm and cozy inside. I put the bed linens washing machine. As I did so, Mimi made breakfast for me, telling me to come and eat before it got cold. I didn‘t have a chance to change out of the couche-culottes, and Mimi seemed to forget that I needed to. So I sat down and began to eat.

"I‘ve already eaten, Evelyn, and I need to get going in a few minutes. I think I might go home after work and catch up on my mail and messages. Just in case I don‘t make it back in time, please put the pot roast in the oven" giving me further instructions.

"You will be alright without me, won‘t you?"

"Of course, Mimi."


She went to her room and came back out as I finished breakfast. She had added a gold necklace and a scarf and was carrying her coat and purse which she put on a chair in the hallway.

"Come sit with me for a moment, Evelyn" she said, motioning me to the couch in the formal living room. I sat, gathering my robe around me. She sat close, facing me. She smelled nice, having put on perfume. My morning coffee was having an effect, and I would soon be in need of a toilet.

"Are you sure you‘ll be alright by yourself today?" she asked with concern.

"Yes, Mimi, I‘ll be just fine" I replied softly.

"I can probably find someone to watch the gallery for me and stay with you if you want."

"No, Mimi. Honest, I‘ll be fine."

"It‘s just that… well, I feel bad about the things I said to you this morning. You know… about being… delicate and inadequate and all that. I just want to make sure that you don‘t use my comments as an excuse not to dress up today; I think it‘s important that you do dress up in ladies things, especially today. I think it will calm your emotions, don‘t you? Promise me you will?"

As she said these things to me, I passed a little bit of water — I was beginning to discover that I could just relax and trust the couche-culottes. It was quite a memorable little moment — she reminding me how delicate and inadequate I was as I wet myself, trying to hide that I was passing water. What more evidence was needed that I was delicate and inadequate than to be sitting on the couch, dressed in a silk surah robe, chemise, bustier, tap panties, stockings, and stiletto-heeled boudoir slippers, while wetting myself?

"Yes, Mimi. I‘ll wear a dress today, I promise" I lisped,

"Oh, good, I feel better now. I think maybe you should wear some of your mommy‘s things today. After all, she has such pretty dresses and things, and I know she would be happy to have you wear them."

What an odd suggestion, I thought, since I had my own wardrobe. But I didn‘t comment on it, simply replying "Okay, Mimi."

She leaned over and kissed me on the cheek and rose to leave. Her last words were "Be sure to wear your couche-culottes when you‘re in bed."


I mulled over our conversation as I sat passing a weak little stream of water. I rose and stood in front of the mirror and slowly parted my robe as a quiver went through me. I relaxed and let it flow. In my stillness, I thought about my day. I would first have to deal with my couche-culottes, but then it would be up to my boudoir to bathe and dress. Yes, perhaps I should wear some of my mother‘s things. I had only one chore for the day; to attend to the laundry and ironing.

My reverie was broken as I saw, reflected in the mirror, an express package van coming up the driveway. I ducked out of site, peeping through the organza curtain as the truck stopped and the driver stepped out. He retrieved a fairly large and long cardboard box from the back of the truck and carried it to the front door. All I could think about was whether he would require my signature — there was no way I was going to open the door in my current state, all dressed in silk surah and wet beneath. But he set the package down, rang the doorbell (causing me to jump, even though I was expecting it), then turned and left.

As soon as the van was out of sight I opened the door and brought the package inside. It wasn‘t as heavy as it looked. It was from Auntie and was addressed to me. I went to the kitchen, retrieved a knife, and cut the box open. Breathlessly, I parted the top of the box… could it be? The first thing I saw was white ribbed cotton blend fabric — it looked like a camisole. I slid my hand down between the contents and the side of the box — all I could feel was fabric. Auntie had sent more clothes! What delicacies awaited me inside? If it was anything like her last package, I was in for a wonderful day! I immediately decided I would wait to unpack the contents; I‘d take the box to my room and unpack it, perhaps after bathing, perhaps after elevating my senses.

I cleaned myself up in the downstairs bathroom, rinsing out the wet terrycloth panties and pad cover, disposing of the pad, and donning the dry pair of thick terrycloth panties. Then I went upstairs with the box, set it on the loveseat, and began my morning bathing.

I started with a shower, washing my hair and using my favorite conditioner. After towel drying my hair, I dried it nearly dry with the hair dryer, set it in warm curlers, put a plastic cap over it, and drew a bath with scented bubble bath. I bathed while thumbing through a new clothing catalog, admiring the dresses and the models. After bathing, I applied my various lotions and creams and scented dusting powder, then sat at my vanity in my terry bathrobe and applied my base makeup, waiting to see what colors I‘d be wearing before applying highlights. I retrieved some candles from around the house and set them up in the boudoir. I put together a tray of cheese and crackers and a bit of sherry and brought them to my boudoir. After drawing the curtains and switching on the tasseled lamps my boudoir took on a most romantic glow. I put my favorite classical music on the stereo.

As Mimi had suggested, I wore something of my mother‘s — her beautiful and diaphanous pink chiffon robe and nightgown. Then, finally, I went and heightened my senses with my hashish, then opened the package from Auntie.


On top of the white ribbed cotton was an envelope from Auntie addressed to me. Inside were an unlabeled CD and a note:

My dearest Evelyn:

I know you said you didn‘t want these, but Suzanne and I came across these the other day and thought you might have changed your mind. Suzanne and I are up north at a retreat and can‘t be reached. I‘ll call you next week.

Much love,

Aunt Beverley

PS: You are so cute and lovely in these pictures!

I knew the CD contained the pictures they took of me in the Susan Lane bridal gown and the powder blue georgette dinner dress. There would be time to peruse them later.


Beneath the note was a white ribbed cotton camisole and roomy pajama bottom, the cotton soft and warm, almost like chenille. The camisole was adorned with white machine lace, as was the hem of the pajama bottom. At first, I was a little disappointed — I was anticipating something very feminine. But I realized that I needed something practical, and the set certainly was.


Beneath the cotton set was another handwritten note on pretty pink stationary.

My dearest Evelyn:

I thought you might like this poet‘s blouse. It came into the shop and I immediately thought of you -- and how you like to write poetry. I thought you‘d like having a real honest-to-goodness poet‘s blouse to dress in when the muse strikes. If not, then your mother might like it for her wardrobe — it would go great with the taffeta skirt and princess petticoat that I‘m also sending. I‘m including some very nice vintage lingerie that we recently acquired and a pretty dress for autumn. Oh — and a really cute sailor‘s dress.

Much love,

Aunt Beverly


Beneath the note was a folded piece of beautiful antique white fabric.

"Oh my" I whispered, in between titches. Out came the poet‘s blouse. It was made of exquisite synthetic georgette, lightweight with a sensuous fluid drape. There were three tiers of ruffled Chantilly lace on the deep shawl-like neckline and cuffs. At the joining of the neckline was a large loosely tied bow, its streamers embellished with lace. Each tier of the sleeve cuffs was also decorated with a thin ribbon tied in a bow. The sleeves were full, billowy, and extra long. It appeared as if the sleeve cuffs would cover most of my hand. Each sleeve had a thin panel of lace running down its length with pleats on either side. The blouse itself was long — almost chemise length. The georgette was sheer and would show whatever lacy camisole I chose to wear beneath. "Oh Auntie…" I whispered.

I lay the blouse on the bed and went back to the box. The next item was a chemise made of the same georgette as the blouse and profusely decorated with the same lace — a deep chevron from the breasts to the midriff, and four inches of lace at the hem. The label was the same as the blouse — this was a matched set. The cut of the chemise was such that much of the lace of its bodice was exposed by the neckline of the blouse. I placed the chemise next to the blouse and stepped back.

Such heirloom treasures! The blouse was so utterly feminine. And the matching chemise! This was no androgynous poet‘s blouse, oh, not at all. "…when the muse strikes…" indeed, I thought.

Back to the box I went. The next little treasures were a pair of fingerless crocheted gloves in antique white, a long rectangular lace scarf, and a wide black velvet neck choker with a black and white cameo of the profile of a young lady, her hair done up,

Then an over-the-knee length black taffeta circle skirt, full six gore, black, with a shimmering moiré pattern weave, with a wide black satin sash that buckled in the back with a big black satin bow and a foot or more of the sash streaming beneath the bow. Then another treasure that made me cry with delight — a three layer white princess petticoat meant to pouf out the taffeta skirt. The middle layer was made of yards of white tulle netting, sandwiched between two layers of white organza. The inner and outer layers were trimmed with three inches of scalloped accordion-pleated lace. The waistline of the petticoat had two drawstrings about two inches apart, and I figured out that they were to allow for two different lengths. If the upper one was used, the petticoat would show past the hem of the skirt. If the lower drawstring was tied at the waist (and the remaining fabric above folded down), the petticoat wouldn‘t show. These were placed gently on the bed next to the blouse and chemise.

A shoebox was next. Inside was a pair of three inch stiletto heeled open-toed pumps. They were black and of basically the same taffeta fabric as the skirt, with a black satin bow at the instep.

Next in the box was a white sailor‘s blouse in a lightweight synthetic georgette crepe. It was such a classic — the V-neck and navy blue scarf, the little caplet, trimmed with navy blue, the three-quarter sleeves also trimmed with blue, and a blue-trimmed elastic waistband. And then two skirts, one navy blue and the other white, both intermission length and pleated, made of the same georgette crepe. Beneath the sailor‘s dress was another box containing a white straw hat, the brim turned up, the small crown decorated with a navy blue band that tied in the back with a bow with long trailing ends.

"Oh…" I gasped, laying the ensemble on the chair.

Then another treasure — a velvet burn-out wrap dress in a deep burgundy with an autumn leaf motif. This I hung on the closet door. It was gorgeous — a charming day-to-dinner dress for the autumn season, exuding well-heeled casual elegance.

More treasures followed — a blush peach negligee, the bodice all lace and the asymmetrical hem a foot of delicate lace, along with a matching lace jacket. Finally, there was three pair of delicious high-cut panties, all the same except for their pastel color, all in a shimmering jacquard satin, trimmed with white lace, and several pair of seamed nylon stockings, including ones in black that I‘d wear with the new ensembles.

There was no doubt — I‘d be dressing in the poet‘s blouse and taffeta skirt ensemble. I assembled the rest of the dressing: the Jane Woolrich white crepe de chine foundations and dance pantie, tulip flutter panties, the high-cut panties that I had just received, and a pair of lacy briefs. Black seamed stockings completed the underdressing — oh how I wished I had garters. I added the big black satin hair bow of my mother‘s and the black velvet choker with the black and white cameo. I wasn‘t sure I‘d wear the cameo — the blouse really didn‘t need anything. The set of pearls would be fine. I might use the lace scarf as a hair band rather than the hail bow. I borrowed a gold ankle bracelet with a drop of pearls at the clasp from mother‘s things.

I turned the lights up to complete my makeup. Since the ensemble was pure black and white, I‘d let my makeup provide color — a porcelain geisha look, with full pouty lips in deep red. After completing my makeup, I lit the candles and turned all the lights off. I would dress in soft candlelight. After dressing, I‘d heighten my senses a bit more and turn the lights on, then present myself to the dressing mirrors. I would be quite a moment.

I disrobed, patted a bit more body powder, and donned the fingerless lace gloves that Auntie had sent. I sat at the dressing table and carefully donned my freshly laundered foundations and new stockings, finishing that phase of dressing with sprays of perfume from my crystal atomizer bottle with its tasseled bulb. I was ready for the petticoat and chemise. I almost swooned when I donned the princess petticoat — the rustle of the organza and tulle thrilled me to my very core; a sissy in a princess petticoat.

More enchantments followed; the chemise and blouse. I first donned a fine mesh hood of mothers meant to be worn when drawing a garment over one‘s head. It prevented my makeup from being smudged as well as preventing makeup from getting on the blouse. I paused to smooth out the chemise, blouse, and petticoat. I decided to wear the lace scarf as a head-band rather than the black hair bow, and after getting it just right, I turned my attention to the taffeta skirt. The rustle of the skirt sent shivers through me. It took a bit of time to dress in it, as I had to draw it over the voluminous petticoat. I had difficulties; the skirt waist, even unzipped, just wasn‘t large enough to take the entire petticoat hem, and required several false starts drawing it on. But I finally managed to draw it on, zip it, and fasten the sash with the bow. Then finally, I slipped into the new heels. I could see myself in the mirrors, but just barely. The three candles I had lit only gave enough light to dress myself.

With my dressing done, I sat back down at my vanity, lit some candles so that I could see myself better in the mirror, and then took even more hashish; I was so high; I probably partook too much, as thoughts of utter shame and humiliation swept over me.

I took stock of myself. Here I was; a fragile little wisp of a boy, with fine delicate features and clear creamy alabaster skin. My long brunette hair with its beautiful natural wave, my vivid blue eyes with long eyelashes — I was just so very fetching — the only child of a very wealthy family, spoiled, living in a manor, crossdressed by my mother, pampered and cosseted and crossdressed by my French nanny who thought me delicate and inadequate. And here, in the deliciously feminine bedroom that mother decorated for me, sitting at the antique dressing table, my face painted, my lips deep red, my cheeks blushed, sipping sherry from a crystal flute, soft romantic classical music on the stereo, wearing the finest dainty underthings that my Auntie sent me, a splendid chemise, an exquisite blouse, an utterly feminine taffeta skirt and princess petticoat, expensive jewelry, and flirtatious high heels. My mother wanted a daughter. My Auntie, I thought, was lovingly providing succor to her delicate, frail, and misunderstood nephew. My handsome French nanny was keeping me dressed while my mother was away, subduing and controlling me with her insistence that I wear couche-culottes because of my bedwetting. I should have felt shame and humiliation; what an unsuitable boy I was! But, as Mimi had said, I made a fine young lady. I gazed at my reflection in the mirror, fondling my hair and the lace of the exquisite blouse with my lace gloved hands, reaching deep into my thoughts. I felt so fetching, so delicate, and so utterly feminine. The emotions that were rushing into me and consuming me blended together into a pure sensual state; every one of my senses was charged.

I stood slowly, not wanting to faint from the rush of the hashish. I was almost panting, my padded breasts rising and falling beneath the blouse. I turned on the table lamps and presented myself to the mirrors.

Oh my.

I could barely breathe, it seemed. I turned slowly about and posed.

I felt the rustle of the skirt and petticoat — taffeta, organza, and tulle, the lace of the petticoat showing two inches below the skirt. I was building up to the moment of purest pleasure and joy. In my nest of exquisite femininity, the nest that mother had made for me, I stood at the mirrors, and then sat in the chair, my stocking‘d legs together, angled to the side, revealing the petticoat. I was titching loudly, crying out, and saying shameful things as I made slight movements in the chair that sent waves of bliss crashing over me. The moment came when I crossed my legs, gathering folds of taffeta, organza, and tulle in my lap. Nothing interfered with the moment — no worries of anyone hearing me, no thoughts of shame — just a loud moaning cry of "Oh Evelyn!" as my contractions intensified and the grand mal orgasm shook me.


I sat for the longest time, waiting for my daintie to stop quivering and relax. I had made sure my panties were well-protected, so I wasn‘t too worried about sullying them, although the outburst I had just experienced would probably require some of my panties to be laundered.

I began to undress — I had other things to try on, and besides, the poet‘s blouse and taffeta skirt was a dressing to reserve for a special occasion. After removing my various panties, I donned a pair of the thick couche-culottes terrycloth panties in order to absorb my post-creaming; another good use for the terrycloth panties.


I tried on the velvet burn-out dress; a perfect day-to-dinner dress, not too formal but classy. From my mother‘s things, I found a pair of leather burgundy kitten-heeled pumps and a matching over-the-shoulder purse, perfect accessories for the ensemble.

Then I tried the sailor‘s dress, first changing into the blue negligee and matching foundations with blue stockings. The bodice of the blue with white lace negligee showed from beneath the white georgette crepe of the blouse, and the movement of the pleats on the skirt was so very feminine and graceful. But it was the straw hat with its blue ribbon trim that really defined the ensemble. It gave it that vintage little girl look. Pearls were just the right touch, adding a bit of a grown-up look to the ensemble. The skirt was the same length as the negligee, which meant that the white lace at the hems of the negligee would occasionally show when I moved or sat with my legs crossed. I wondered what would be revealed by the skirt if I went without the negligee, so I undressed and replaced the negligee with the chemise and donned the white skirt. Now the white lace of my tap panties and chemise showed beneath the semi-translucent white georgette of the skirt. "Oh my" I thought to myself, "…one simply must wear a petticoat with this skirt, or one‘s panties will show."

My trance was broken by the phone ringing. The caller ID said "international" — it had to be my mother. I sat down at my vanity and answered. As I expected, it was her.


After catching up about her trip, there was a pause in the conversation. Then mother asked "Now, tell me about what you‘ve been doing, sweetheart."

"Oh, nothing much… just school and stuff" I replied, knowing that she was waiting to hear more.

"Dear? I know you got the note I left you and you know I‘ve talked to Mimi. I wanted to talk about your dressing up as a girl. You have been dressing up, haven‘t you?" she asked coyly.

"Uh huh" was all I could think of to say.

"Well? How are you doing? Are you having fun? Mimi said she was going to try and have you dress up every day. Have you?"

It was no use trying to gloss it over; the time for denial was far past. I let myself have a silent sigh, then in a perkier voice replied: "Yes, mommy. I‘ve dressed up every day this week — Mimi‘s been really helpful and we‘ve both had fun." I paused for just a moment and added: "I… I like it, mommy."

"Oh, that‘s wonderful darling, just wonderful. So you and Mimi are having fun? I‘m so glad. She‘s such a wonderful person, dear, and I‘m so delighted you‘re getting to know her better. She‘s been encouraging me all along to help you emerge, to recognize the difficulties you face and, I guess, my own inhibitions. She really knows what‘s best for you, best for both of us, actually. So, tell me…" she finished, changing the subject slightly, "…do you like your new room?"

"Yes, mommy; it‘s really nice… beautiful. I like it a lot." My response was absent-minded for I was thinking about what she had said about Mimi — there was much more to her and mother than met the eye.

"Where are you now, dear? Are you dressed?" she asked.

"Oh, I‘m in the study, just doing my homework" I lied — I wasn‘t going to tell her I was in my boudoir primping. I was now standing at the cheval mirror, holding my skirt out with one hand and holding the phone in the other. I answered her second question, again lying: "I‘m wearing that nice turtleneck sweater you bought me and the gray skirt." I didn‘t want to tell her how I was really dressed since I‘d have to tell her all about the package Auntie had sent. No mention of Auntie had been made, and I wasn‘t going to bring it up unless she did.

"I bet you look beautiful. Speaking of sweaters, dear, that reminds me: I had a chance to browse through the most wonderful little shopping district today — a little alleyway actually" she said with enthusiasm. "It has all these little shops and boutiques world famous for their sweaters and furs — beautiful things in wool and cashmere with some angora and mohair too, lots of different designers and styles… really classy things. I saw this beautiful sweater dress in one of the windows, along with skirts and sweaters and such. It‘s very upscale and expensive, but quality is worth it. I‘m going back tomorrow afternoon and I want to buy us some things — they can ship anywhere in the world."

"Oh… that sounds wonderful mommy. I‘d like a nice sweater dress. It‘s getting cold here."

"Then a nice sweater dress you shall have, dear. How about some skirts and sweaters, too? I saw this really cute pleated tartan skirt and a jumper dress that I want to get you, along with some cashmere tops."

"Wow, that would be really nice, mommy" I replied.

"This will be exciting, shopping for you" she added. Her voice softened and in a conspiratorial tone, she said "And when I get back, maybe you can wear them when we go shopping together."

"Uhh… okay, mommy…" I stammered.

She said a few things about her itinerary and then said our goodbyes.

After I hung up, I stood at the cheval mirror, recalling the conversation as I twirled my hair with my fingers. I thought about the relationship between Mimi and mother. It was Mimi who had convinced mother to ’let me emerge‘. It sounded like mother had reservations, but Mimi persuaded her otherwise, converted her, and convinced her that I was more suited to be her daughter. I dallied on the part about how she was going out shopping for me and buying some very nice sweaters and skirts and dresses, and how I might wear them when she returned home and took me shopping. And then, finally, how Mimi knew what was "best" for me. Was having me wear couche-culottes really "best" for me?

There seemed to be no escape from being crossdressed, even if I wanted to; not from mother, certainly not from Mimi, or probably even Auntie. They were turning me into a girl, or something like it — I wasn‘t sure. I felt smothered. But I could worry about all that later; for now, I felt warm and safe and secure.

Musing over these thoughts, I undressed from the sailor‘s dress, donned the white fox stole, and went to my mother‘s room. After all, Mimi had suggested I wear some of her things. I put on my mother‘s diamonds, including the tiara, and slipped into a pair of her blue four inch heeled sling-back pumps. From her scarf drawer, I selected a blue floral pattern silk scarf that could be scarified like the beige chiffon scarf. Back in boudoir, I laid the mink throw across the bed, turned the dressing screen around so that I could watch myself in its mirrors, and had an exquisitely slow pillow ride in full view of all the mirrors, the diamonds sparkling occasionally, my white fox stole slipping from my shoulders, thankful that the house was empty and the neighbors were far away for my cries were rather shrill and piercing.


It was mid-afternoon when I came downstairs dressed in the white ribbed cotton camisole and pajamas, overlaid with my slate blue silk and cashmere robe. I liked the set, soft, warm, and feminine, but practical at the same time. I was glad Auntie had sent it.

I had laundering and ironing to do and I set up the ironing board in front of the television. When I got to a stopping point, I took the CD that Auntie had sent and sat at the computer in our study, reminiscing about that unusual and wonderful day, amazed at the young beauty in the Susan Lane bridal gown staring back at me — could that possibly be me?

I was doing some research on digital cameras when I saw a car pull up into our driveway. It wasn‘t Mimi, so I moved away from the desk and positioned myself by the study window, hidden by the drapes, and peeked through the little gap between the curtain and the wall. The car stopped and out stepped Ms. Hunter.

She was nicely dressed in a burgundy red wool pencil skirt, a tight-fitting white turtleneck sweater, high-heeled red pumps, a red hair bow, and a white wool trench coat with a pretty red scarf with an autumn leaf motif beneath the lapels. I could see that she was wearing makeup and her lips were glossed in red. She was most definitely not dressed for school (she would have driven the boys in her classes insane!). She was all done up as if going out on a date or something. Standing behind the curtain, I watched as she approached the door; she walked with small graceful swishing steps. She rang the doorbell and I waited, peeping through the window. She rang again, went back to her car, sat down and wrote a note, then came back to the door carrying a manila folder with the note clipped to the outside and set it outside the door.

When the coast was clear, I retrieved the folder. Inside was a handout of study questions for an upcoming test in her class, as well as a list of readings for my government class. Then there was her note:


Dear Evelyn:

I know you‘ve been ill and I just came by to see how you are, knowing that you‘re by yourself. Here are some class notes from this week. Let me know if you have any questions — I‘d be glad to tutor you.

Sincerely; Vanessa

At the bottom of the note was her phone number.

I stared at the note — was she was making a pass at me? What if I had answered the door (as a boy) and she came in? Had she dressed up because she thought she might get to ’tutor‘ me today? (Of all the students at school, I was the one in least need of tutoring.) There was no way I would call her, of course, not with Mimi around, not with their agendas.


I returned to my laundering. It was time to put the pot roast in the oven. Mimi called to remind me and said she‘d be returning around six thirty. That gave me enough time to finish the laundry, dress for dinner, and set the table.

I had to decide on a dinner dress. My first thought was the velvet burn-out dress Auntie had just sent. But I decided against it, opting to wear something of my mother‘s as Mimi had suggested. Mother‘s conversation about buying me a sweater dress got me thinking about the oatmeal colored ribbed angora and lambswool sweater dress that my mother had put in the bureau; V-neck, with mauve trim at the neck, cuffs, and hems, with a long matching mauve waist sash.

After a sponge bath, I removed the more dramatic makeup I had put on earlier and powdered myself. For foundations, I wore the side-zipper all-in-one girdle — the dress was tight fitting and the girdle would lift my derriá¨re and flatten my tummy. My stockings were white silk. For daywear, I chose the camisole, pettislip, and dance pantie set in lingerie pink with ivory Venetian point lace trim and embroidery. I borrowed some my mother‘s artisan jewelry — a necklace with big beads made of faux ivory, with a matching bracelet and disk earrings. I added some bangle bracelets of mauve and ivory Bakelite. The pair of pink and cream two-toned pumps rounded out the ensemble.


By the time Mimi arrived, I had the table set for us. She greeted me warmly and asked how my day went. She had me do a few turns for her and remarked "My, Evelyn, but you have such a nice figure. Sure, you could use a little more padding around your hips, but honestly, I‘m surprised."

During dinner, she brought up the fact that the cleaning service was coming over the next day, around nine-thirty. Their usual time was Tuesday afternoon when I was at the library, but they had to reschedule. Mimi said she‘d have to be at the house to let them in and give them a few instructions. She said they would be in my room to vacuum, clean the bathroom, polish the wood and mirrors and that I would have to ’tidy up‘ before they came. Then she suggested that we should go for a drive in the country. The fall colors were just past their peak, she observed, and she wanted to visit a dairy she knew that made good cheese (her French background meant she was always on the hunt for good cheese) and had a delicatessen that sold all sorts of good cheeses, breads, and meats, made great sandwiches, and had a nice picnic area out back. The weather was supposed to be sunnier and warmer and we could have a picnic lunch — and we would probably have the place to ourselves.

"Oh, and Evelyn? I mean for you to go with me as a girl, just in case you weren‘t clear on that."

"Uhhh…" my head spun. The only other time I had gone out (except for the brief drive home on Tuesday night) was with Auntie and Suzanne, and that was back in San Francisco where, as Auntie had said, no one would recognize me. This was entirely different.

Mimi sensed my hesitation and said "Don‘t worry about being seen, Evelyn. You‘ll be in my car, not your mommy‘s. We‘ll be on the back roads and I‘m a careful driver. You know it‘ll do you good to get out of the house."

I couldn‘t argue with her logic. I felt a chill — I was stepping out again! "I guess you‘re right, Mimi. It would be good to get out of the house. I have been cooped up, haven‘t I?"

"Yes you have, dear. You need to become comfortable going out as a girl. This is a good way to start, don‘t you think?"

"But what about the cleaning ladies?" I asked, suddenly realizing that I would be all dressed up when they arrived.

Mimi pointed out that the last time I met the cleaning service ladies was months ago, and that was only in passing. It would highly improbable that any of them would recognize me as the boy who lived there. "And so what if they do?" she asked firmly. She said she‘d introduce me as mother‘s niece who was staying for a while, which would explain the lived-in guestroom. "You‘ll do just fine, Evelyn. It‘ll be fifteen minutes or between the time I let them in and when we leave. All you have to do is sit in the living room and look pretty."

It was settled; I couldn‘t see any real reason not to go out. Then Mimi asked what I thought I should wear. That reminded me that I had yet to tell her about Auntie‘s package.

"So, your aunt sent you some new dresses and things?" she asked coyly. "My, but you are a lucky lady. As I‘ve said, Evelyn, I don‘t know much about your aunt, but it‘s very obvious that she thinks you should be dressing up. Have you talked to her about it?"

"Not really, Mimi. She sends these things to mommy — they are all things that come into Auntie‘s second-hand store." That was, of course, the ruse. Given the note Auntie had included in the package and all our past history, it was very obvious that Auntie meant the things for me. I wanted to drop the subject so I told her that maybe the velvet burn-out dress would be suitable for our excursion.

"Well, after dinner, you‘ll have to show me everything she sent."


As I began to clear the dishes, Mimi said she needed to relax and was going to take a bath in mother‘s bathroom. She went to her room and reappeared a few minutes later in her black ballet dress and tartan robe, carrying a few bath items. "Let‘s go see what your aunt sent."

It took about a half hour for me to show her everything. She was most impressed. The poet‘s blouse and taffeta skirt were "very special" she said and dropped the suggestion that we should have another dress-up day, just like we did yesterday.

While she took her bath, I did my nighttime routine of applying lotions. I donned my new blush peach negligee and matching lace jacket. And, of course, the usual underthings: the white satin bustier with the white cotton stockings, and the couche-culottes with the pink plastic panties. I applied lots of lotion to my pelvis, derriá¨re, and daintie, quite enjoying myself, then dusted myself and the thick terrycloth panties liberally with baby powder. Knowing that the morning would be a bit hectic getting ready to go out, I wasn‘t going to wet myself that evening, but I still had to wear them because Mimi would check.

Mimi came to say her goodnights, dressed in her black lace over white satin one-piece halter top pantsuit and her blue checked robe. She told me that I looked ’ravishing‘ in the new nightgown. She checked that I was wearing the couche-culottes. I had trouble falling asleep because I was nervous about our excursion and meeting the cleaning crew. But a nice little creaming relaxed me.


Friday

I woke early and had showered and washed my hair and was downstairs making coffee and breakfast when Mimi woke up. She was tickled that I was up so early to get ready. She asked if I had any problems with bedwetting.

"No, Mimi — I did fine last night."

"Really? I would have thought you might have been nervous and that would trigger a bedwetting."


I had already decided on the burgundy velvet burn-out wrap dress for our excursion. I didn‘t have any burgundy lingerie, so I went the pink and gray lace foundations and the muted lingerie pink with ivory Venetian point lace trim camisole, dance pantie, and pettislip. Black stockings seemed best.

I was dressed in my foundations and daywear, my makeup mostly done, when Mimi knocked on my boudoir door an hour before the cleaning ladies were to arrive. She was wearing a tea-length black pleated wool skirt, a claret red cashmere twinset, gold jewelry, and a nice scarf gathered with a gold clip.

Together we made my bed and she made sure all my pillows were fluffed and the heart-shaped boudoir pillow was in the center of the pillow collection. "Let‘s make sure the maids know what a special young lady you are" she said, hanging the lilac chiffon peignoir on the outside of the dressing screen.

I finished dressing, borrowing mother‘s pair of leather burgundy kitten-heeled pumps and the matching over-the-shoulder purse. The last touch was a black velvet jacket of my mothers. It took a while to find just the right jewelry. I swept my hair back and fastened it with the antique silver filigree hairclip and matched it with a multi-strand silver necklace with an onyx clasp. For a final little touch, I wore an antique white lace scarf under the lapels of the jacket. Although the weather didn‘t require it, I would bring my mother‘s natural mink coat just in case the weather turned. My final act before leaving my boudoir was to pack my purse with things I‘d need for the day.


Downstairs, I nervously waited for the cleaning ladies. Mimi had me practice a little bit by having me stand and offer my hand and saying a few words of greeting in a soft voice. Mimi had packed a wicker picnic basket that was waiting by the door.

The cleaning ladies arrived and my heart was pounding. There were two Hispanic ladies and one Caucasian lady that I recognized. Fortunately, Mimi led them immediately to the kitchen and they barely noticed me.

And then we were off. At first, I slouched down in my seat, but as we made some distance from home, I started to relax and enjoy the ride. I was doing it! I was going out dressed as a girl. It was nice to get out into the fresh air. The route Mimi was taking was unfamiliar, so I could entertain myself a little by taking in unfamiliar sites. The fall colors were beautiful. Somehow, the conversation turned to ’passing as a girl‘. Mimi first apologized, realizing that she hadn‘t yet given me any pointers but adding that I really didn‘t need any and that she was a lousy teacher anyway. She gave me some shallow advice on walking — "Hold your head up, take smaller steps." I asked her about telltale signs, like my figure, my Adam‘s apple, and things like that. She began by complimenting me on my skin and hair, saying that was near the top of the list — my skin was so soft, clear, and ’creamy white‘ and my hair was ’luscious‘. My hands and feet were small and that really helped the illusion. My Adam‘s apple, although discernable, wasn‘t big enough to break the illusion. She did mention that she had heard that there was a simple operation to reduce its size. She ended the conversation by saying that perhaps my mother could investigate hormone therapy and a bit of cosmetic surgery for me.

"Oh, I‘m not ready for that, Mimi — no way" I replied. I wasn‘t ready for such drastic measures.

"Well… not yet anyway. See how you feel about it in a few months" she replied gently.


We arrived at the dairy. The delicatessen had a few cars parked out front. We drove around back to the picnic area and parked the car. There was no one else there. While Mimi went inside to buy some cheese and sandwiches, I unpacked the picnic basket she had brought. There was a checkered tablecloth, plates, napkins, utensils, a bag of pretzels, and a bottle of Chardonnay and two wine glasses.

She took a while, but I wasn‘t nervous. Eventually she came out and we ate. She poured me a glass of wine, telling me it would help me relax. There was still a bit of fall colors out. She had brought her camera with her and took a few pictures of me against the backdrop of a large maple tree.

After lunch, I needed to use a restroom. Mimi said there was restroom in the store that was right next to the back door, and she walked over with me. I blushed as I entered the store, a couple of people saw me, but I got in and out of the bathroom without incident. I did spend a minute or so freshening my makeup.


Back in the car, Mimi said she had an idea for us. We were less than a half-hour away from a regional mall. "Let‘s go look at some dresses" she said merrily.

I was floored. "No way, Mimi!" I cried "I‘m… I can‘t go out like this!" I whined.

We were already on the road when she made the suggestion. We continued driving and bickered with each other as we made our way towards the mall. For every argument I had against going, she had a counter-argument. Finally, she put her foot down and declared that I was going to the mall and I was going look at some dresses, perhaps try some on and maybe purchase some. She offered that we‘d go to the mall and park as close as possible to the entrance to Macy‘s that opened into the ladies sportswear department, then go inside and browse the dresses. If I became too uncomfortable, we‘d leave. She informed me that it would be good for me, that I had to start ’stepping out‘ more, and she‘d be there to protect me. She reassured me time and again that it would be alright.

When we arrived thirty minutes later, I was already in a panic. My heart sank when she found a parking space close to the entrance. I was hoping she wouldn‘t find one and we‘d just call the whole thing off.

My heart was pounding violently and my ears were ringing as we exited the car and made our way to the entrance. Someone opened the door for us and we stepped inside to the ladies sportswear department. Mimi took me by the hand and immediately led me into the racks of dresses. "Just relax and have a look, dear".

I began looking through the racks, parting dresses with my red polished nails, making furtive glances around me. I had been looking for just a couple of minutes, just starting to calm down, when I saw a schoolmate of mine with her mother coming towards us. ’What the hell are they doing here?‘ I thought. "Mimi!" I whispered in panic, telling her who was coming towards us. "That‘s Jill and her mother, Mrs. Walker. They‘ll recognize me for sure!"

Mimi took my arm and led me back to the door, saying "stroll, dear, don‘t run."

Back outside and into the relative safety of our car, I let out my breath. "That was close" I said.

"No it wasn‘t dear. You did fine. We‘ll go now before you faint" she said with a grin. A minute later, she apologized, saying "I guess you really aren‘t ready to go out, are you? I‘m sorry. We‘ll take it much slower. Perhaps we‘ll just wait until your mommy comes back. Wait until you‘ve become more comfortable. You were right about this Evelyn… I should have listened to you. I‘ll make it up to you, okay?"

We stopped by a florist and I waited in the car while Mimi went inside and got fresh roses for my boudoir. "One more stop before we head home. Are you doing okay? Do you need to go to the bathroom?" she asked when she returned to the car.

"I‘m okay for now, Mimi. What‘s the next stop?"

"It‘s the Pheasant Run Inn. I want to pick up a flyer on their Halloween party. You‘ll be able to use the restroom there."

I had been by the Pheasant Run Inn a couple of times. It was an elegant old Inn situated along a river, known for its restaurant and as a place to host events, mainly weddings. Its grounds were immaculate. As we drove, Mimi told me that their Halloween party was quite an event which she and my mother had attended a few times when I was younger, which I vaguely recalled.

"It‘s quite fun. There are prizes for various costume categories and everyone wears costumes." I gulped when she added "I was thinking that you and I could go. It‘s a perfect opportunity for you to dress up and go out."

Twenty minutes or so later, we pulled into the parking lot and parked near the side entrance. There weren‘t many cars around. I would have waited in the car, but I really needed to go to the bathroom. My heart was pounding yet again as we went through the side entrance. We didn‘t encounter anyone as I clicked on my heels across the wood floor and into the ladies room, Mimi following behind. She was in the stall next to me and it was disconcerting to hear her undress and use the toilet. After checking ourselves in the mirrors, she led me into the lobby. I was relieved to find that the lobby had lots of nooks and alcoves and I was able to sit hidden away in a comfy chair as Mimi went to the front desk. A minute later, she returned carrying a flyer and a photo album of past Halloween parties.

"Here, take a look, dear" she said, sitting down next to me and leafing through the photo album. Most of the photos were of couples, their costumes elaborate and over-the-top. Most of the couples were the same sex and predominately female. There were a couple of photos of guys in drag; not trying to be feminine, but gross caricatures. It began to dawn on me that the revelers were mainly gay and lesbian that would be more accepting of a crossdressing boy. They flyer described the party and the packages they had available, such as a room for the weekend plus dinner before the party.

"See, Evelyn — wouldn‘t this be fun?" she asked.

"Uh, sure… maybe" I stammered.

"It‘s alright — you don‘t have to decide now — we‘ll take the flyer home with us." She returned the photo album to the front desk and we left, strolling around the grounds a bit before driving off to home.


We arrived back after five o‘clock. I had forgotten that the cleaning ladies had been over, and was pleasantly surprised when I went to my room to find everything polished and the carpet vacuumed. The lilac peignoir and robe still hung seductively from the dressing screen. Mimi replaced the flowers, filling the room with the fresh scent of roses.

Soon, we had dinner and I was upstairs undressing and doing my nighttime routine of applying lotions. I dressed in the moonglow blue pajama bottoms, nightshirt, tap panties, and the slate blue silk and cashmere robe. I wore the bustier, stockings, and couche-culottes beneath. I came back downstairs to find that Mimi had changed into loungewear as well, a set I had not seen before; a peach delustered satin nightgown and robe. The nightgown had a halter top and empire waist, the bodice and halter had an off-white lace net overlay as did the wide lapels of the robe. After I complimented Mimi, she said she had brought it from her home Thursday night, along with some other things. It was a different look for her; pink and soft and feminine.


We watched some television, both of us sitting on the couch. I brushed out my hair. When the program she wanted to watch was over, she flipped channels to an infomercial on beauty products and turned down the volume. She then laid a pillow on her lap and invited me to lie down and put my head on her lap. So invited, I situated myself, lying on my side, my head on the pillow facing the television and stretching my legs out on the couch. She began toying with my hair and asked if I had a fun day.

"Oh yes, Mimi, it was fun going out" I purred.

"Except for the little trip into Macy‘s, huh?" she asked.

"Yea — that was nerve-wracking. Sorry I freaked, Mimi" I replied.

"And I‘m sorry too, Evelyn. You‘re really not ready and I think that‘s mostly my fault. I haven‘t given you any sort of tips about acting as a girl. Your mommy will be much much better at that sort of thing; she‘ll draw on her modeling experience. I‘ll tell you what — I‘ll make it up to you tomorrow. After breakfast, I‘ll start your bath and then I‘ll go put on something nice. Then I‘ll help you dress up in that beautiful blouse and taffeta skirt that your aunt sent. We can take some pictures, just like we did a couple of days ago, and then you can go have a nice afternoon nap. You‘ll have plenty of time to dress in something different for dinner if you want. How does that sound?"

As she was telling me this, she continued stroking and fondling my hair. It felt so nice. "That sounds really lovely, Mimi — but you don‘t have to go through all that trouble for me" I purred again.

"It‘s no trouble, Evelyn. I like dressing you up, dear. It‘s a lovely way to bond with you — and it‘s enjoyable to watch how your personality changes."

"Really?" I purred — I was getting a little creamy and dreamy; she was taking strands of my hair and lifting them straight up, tugging just a bit, then letting the strand fall. She was letting her French accent slip, her voice was soft.

"If you don‘t mind, Evelyn…" she continued, "… could I help dress you in some of your more, um, intimate things? Like your brassiere? Because, really dear, the only thing you need to do in privacy is to put on your panties… I can help with everything else. After all, when you were little, I‘d give you baths, right?"

I should have realized what she was asking, but I was just so content and dreamy at that point, so ready to go to my room and play, that I purred "Sure, Mimi, I don‘t mind — if that‘s what you want to do."

"It is, Evelyn" she said, her voice barely audible.

After a half-minute of Mimi absentmindedly stroking my hair, she said "You must be tired dear. Why don‘t you go to bed now?"


I was titching by the time I made it to my room. I was wetting myself a little bit as I made my way to the toilet. After my toilet, I drew on my slightly damp couche-culottes then added lots of lotion all around my aching daintie before drawing on the plastic panties. I was in such a perfect mood for snuggling up to my lacy heart-shaped boudoir pillow.


Saturday

I woke early with nature calling and rose to use the toilet, but I didn‘t completely empty myself. I went back to bed, drifting in and out of sleep as I passed occasional weak streams and wetting myself. Less than an hour later, Mimi knocked on my door and came in. She was still dressed in her peach nightgown and robe. She was carrying a cup of tea for me and put it on my night table as she sat on the bed next to me.

"Good morning, Evelyn. Did you sleep alright?"

I sat up in bed and replied that I slept wonderfully, taking a sip of tea. I detected the taste of Mimi‘s tea mixed with mothers.

"Did you have any problems?" she asked concernedly.

"I… I think I wet myself last night, Mimi" I lisped.

"Are you sure?" she asked, her voice gentle.

"Uh-huh."

"Oh you poor thing… Let‘s check you for wetness then. Go on and sit up, dear" she said kindly, slipping into her heavy French accent.

I sat up on my knees. I was still wearing the pajama bottoms and she told me to pull them down so she could check me. I drew them down slowly. As she had done previously, she fingered the fabric of my panties and the stocking suspenders, starting in the back. And, just like the other morning, she tried to comfort me by saying "You poor thing, Evelyn… having to deal with the shame of your bedwetting. I‘m so sorry… I‘m here to help, dear…"

She was satisfied with her inspection and I sat back down. She continued with her comforting and sympathetic tone, saying "Don‘t take this the wrong way, dear, but I think your bedwetting is just a symptom of your submissiveness."

I blushed and toyed with my hair and the strap of my camisole. I knew a lecture about my submissiveness was now coming, and I wasn‘t going to interrupt — although her words would sting, I found her sympathetic tone comforting. Besides, it was as if she was talking about someone else since I wasn‘t truly a bed wetter.

"I know you probably don‘t like hearing it, but your personality is quite submissive; after all, you‘re dressing up as a young lady, wearing ladies underthings to school and the library, lounging about at home in high heels and dresses, and… wetting your bed. These are all sure indicators of submissiveness. But it‘s alright dear… it‘s who you are, and you have to get past any feelings of shame and inadequacy. You poor thing… trust me dear, it‘ll all be fine. I have a nice day planned for you… we‘ll get you all dressed up just as pretty as can be and then you‘ll feel much, much better, alright?"

"Yes, Mimi" I whispered, my voice quavering as I began to pass water into my moist and warm couche-culottes.

"Good. I‘ll go start breakfast… come down when you‘re ready."

I finished the tea and by the time I came downstairs, carrying a fresh pair of the terrycloth couche-culottes, I was wet and immediately went to the laundry room to take care of my wet things. Mimi had thoughtfully put a carton of baby powder in the laundry room. I removed the wet couche-culottes and plastic panties, rinsed everything out, disposed of the wicking pad, started the washer, then washed myself and applied powder before drawing on the soft dry couche-culottes.

Mimi was in the kitchen, humming to herself as she laid out breakfast for me. I was quiet, thinking about her comments on how I was a submissive little thing. Outside, it was beginning to cloud up, further quieting my mood.

"I‘ll go upstairs and make your bed, dear, and start your bath while you finish your breakfast. Just come on up when you‘re done."


Mimi was waiting for me at the top of the stairs, smiling. Her robe was open, revealing the lacy bodice of her nightgown. "All set for you" she said gaily as she watched me come up the stairs and enter my boudoir.

She had made up my bed; the pillows were all fluffed, the lacy heart shaped satin boudoir pillow in the middle of the neatly arranged mound. She had turned the dressing screen around so that the mirrors were facing the bed and moved the ottoman to the front. The curtains were drawn almost closed. It could have been dusk. Classical music was playing on the stereo. I disrobed, laying my things on the wingback chair, and went to bathe. Mimi had filled the tub with aromatic bubble bath and lit a scented candle. I slipped into the warm water and sighed, then began lathering myself lavender soap. I washed my hair, using the detachable shower head to rinse. Feeling in the mood, I retrieved my stash of hashish and pipe buried deep in the linen closet in the bathroom and partook of just a bit, then settled back into the tub. My thoughts entwined around Mimi‘s ’submissive‘ comments as I relaxed in the steamy hot bath. A wealthy, cosseted, and submissive sissy was what I was, and I was so enjoying it, having a luxurious bath before being dressed for the day by my French nanny.

I dried my hair then put it in hot curlers and wrapped the terrycloth turban around it. I was applying after-bath lotion when I heard Mimi enter my room. She asked how I was doing.

"Almost done, Mimi… I‘m just putting on a little dusting powder" I replied with a lilt.

I tied the terrycloth wrap around me and then donned the plush terrycloth robe. I stepped out of my bathroom. Mimi was sitting on the wingback chair. She was stunningly dressed in the black lace dress that I had brought from her car: it had a squared neckline, three-quarter sleeves, and an A-line knee-length skirt. Around her waist was a wide shiny red belt. She wore black seamed stockings and red leather pumps with a mid-height heel. Around her neck was a red satin choker with a big red rose petal worn on the side. She had borrowed several of my mother‘s gold and plastic bangle bracelets that clinked whenever she moved her arm. She had full makeup and her lips were a deep red. But it was her hair that was most striking — she had applied mousse and brushed it out to give it a good deal of volume; it was no longer a conservative long bob but an untamed and riotous coif appropriate for an evening out on the town.

"Wow, Mimi, you look fabulous" is all I could say.

"Why thank you, Evelyn. You‘re going to look fabulous too when I done with you. Now why don‘t sit at your vanity and do your face while I bring out your things."

I sat down as instructed and began with the whitest foundation cream I had. Mimi was humming along with the music from the stereo. She opened the closet and brought out the poets blouse, taffeta skirt, and princess petticoat and laid it on one side of the bed. She took each piece out individually and took her time laying each one out, giving me time to do my makeup. Then into my lingerie drawer she went, bringing out the white crepe-de-chine garter belt, brassiere, my brassiere sachets, and a pair of French-heel white silk seamed stockings, again bringing out each piece individually. She carefully laid these on the side of the bed facing the mirrored dressing screen. Then back to the closet for the crepe-de-chine dance pantie. Finally, she went back to my lingerie drawer for the crepe-de-chine bikini pantie that matched the brassiere and garter belt, the pair of tulip panties, and a lace-trimmed damask handkerchief.

"I know what the handkerchief is for, Evelyn — I think it‘s a really good idea."

I didn‘t know what to say; I just sat there stunned. She took the panties and the pantie napkin behind the dressing screen. Finally, she brought out the crepe de chine long robe and hung it on the back of the dressing screen.

Seeing that I wasn‘t quite done with my makeup, Mimi excused herself, saying she was going downstairs to fetch some sherry for us. "I know it‘s early in the day for a sherry, dear, but you‘re looking a little nervous. I‘ll be back in fifteen minutes or so — that‘ll give you time to finish making up. Now don‘t put anything on until I get back — remember what you promised last night?" she asked, referring to her request to help dress me in my "intimate things".

As soon as she left, I went to the bathroom and partook of a little more of my stash. I wasn‘t worried about Mimi discovering I was partaking of hashish. I knew there would be no scent if I exhaled out the window. The aromatic candle and bathroom fan would take care of the rest. As soon as I sat back down at my vanity, I started having a little anxiety attack. I looked about the room at the things Mimi had laid out, realizing that I was going to come out from behind the dressing screen in just my panties and the robe and letting Mimi see me in such a state of undress — it was just one more piece of my dignity I was giving up. Then the thought of her helping me into my brassiere and garter belt struck me. It was just too intimate, too sexual, and it scared me.

I tried to calm myself by finishing my makeup, bring my lips out as full as possible with deep purple lipstick. I added to my eyeshadow and mascara and cheek blush. I was done up like a porcelain doll

Mimi arrived, carrying a tray with a decanter of sherry and two small crystal goblets. It took her about half a minute to realize my mood and that something was wrong.

"Is something the matter Evelyn?" she asked concernedly.

"Mimi…" I whined just a bit "…I‘m scared… this isn‘t right…" and then a tear or two came to my eye.

"Nonsense mon chéri" she said, her voice lilting, letting her accent come out more. "Here, come and sit by me…" She sat down on the loveseat and motioned for me to sit next to her. I sat and she put her arm around me. She told me to drink a bit of the sherry to calm myself. I kept my eyes down, not wanting her to see my glazed and dilated pupils.

"There‘s no reason to be scared, dear. For goodness sakes, I‘m not going to hurt you."

"I know, Mimi… It‘s just that… well, it‘s wrong… It‘s just all wrong…" I sniffed.

"What? It‘s wrong for me to help you dress? What could possibly be wrong with that? I‘m not going to do anything inappropriate, Evelyn. You‘re just being silly. Nannies are supposed to help their young lady‘s dress."

"It‘s not just that, Mimi… I shouldn‘t be doing this… you know… dressing in ladies things."

"Evelyn, we‘ve been through this. You‘re a lady, a fine young lady… an oh-so-pretty young lady. Sure, you‘re in a boy‘s body, but you‘re a fragile and inadequate boy, much better suited to being a girl."

"Oh, Mimi" I whined, taking a tissue from the vanity and blowing my nose and dabbing my eyes with another.

"There, there. You‘ll feel much much better once you‘re dressed up. Perhaps it‘ll help if you call me ’nanny‘ while I‘m dressing you. After all, I was your nanny not many years ago, and I bathed you and dressed you then. Now let‘s not discuss this anymore — you need to go put on your panties and the robe."

"Okay, Mimi, I guess you‘re right."

"Of course I‘m right. And call me ’nanny‘, alright?"

"Yes, nanny; thank you, nanny."


I rose and went behind the dressing screen, my ears ringing, my cheeks flushed. I finished the glass of sherry and it did help me relax a bit. I disrobed from my terrycloth things and slipped on the bikini panties, adding the damask pantie napkin. As soon as I nestled the pantie napkin around my daintie, she became aroused and I had to concentrate to make her relax. Then I slipped into the tulip panties. I was glad Mimi had brought them out for me because the bikini was quite immodest. I donned the robe and wrapped it around me and stepped out. Mimi was standing by the bed waiting for me.

I stood facing the mirrored dressing screen, my nanny behind me.

"Now mon chéri, undo your robe" she whispered as she lifted the brassiere from the bed.

"Yes, nanny" I said under my breath. I let to robe fall to my waist, held at my waist by its sash. She stepped in front of me and guided the brassiere up my arms, then stepped behind me, drew it on, and fastened the back. I stood stock-still, watching my reflection in the mirror, barely breathing, trying not to get completely overwhelmed by the sensuality of the moment. The only thing holding me back was that the handsome and well-dressed woman that was dressing me was almost family to me.

The garter belt was next. While Mimi held my robe, I undid the sash. When the sash was undone, Mimi casually draped the robe across the bed. She encircled the garter belt around my waist and clasped it in the back. Then she took one of the suspenders, pulled opened the waist of the tulip panties, and let the suspender fall between my bikini panties and the tulip pantie. She did the same with the remaining three suspenders. She worked quickly and I was thankful she did because it would have been far too sensual of a moment otherwise.

She helped me back into the robe, saying "We mustn‘t let you become chilled, mon chéri. Your stockings are next — sit down at your vanity and I‘ll roll them for you."

I sat and watched as she took one stocking and slowly rolled it for me. She had me lift my leg and she worked the stocking over my foot to my ankle, then whispered "You take it now…"

I reached down and unrolled the stocking up my leg. "Be sure the seam is nice and straight, mon chéri" she said.

"Yes, nanny" I rasped. When the stocking was unrolled, I clasped the top suspender, and then rose from my chair to clasp the back suspender. Mimi helped me by guiding my hand so that the suspender was straight. I sat back down and we repeated the process with the other stocking. "Your legs are so shapely, Evelyn… you‘ve got your mother‘s legs" she told me.

"Now your panties" she said, holding up the pair of crepe-de-chine dance panties. She opened the waist and guided the panties past my ankles and up my calves until I could easily reach them. I drew them up past my knees then stood and drew them on the rest of the way.

"Let‘s let down your hair" she said as I sat back down. She stood behind me and unwound the turban around my head, then began to remove the curlers, letting my hair fall. "You have the most beautiful hair, Evelyn…" she whispered, adding a few more superlatives. When all the curlers were out she fluffed out my hair a bit then led me back to the mirror. Mimi took one of the sachets and stepped in front of me. I made a motion to take the sachet from her, but she refused my offer, saying with a hint of exasperation "Oh, let me do it, alright mon chéri?"

"Yes, nanny" I breathed.

She opened the cups of my brassier and inserted the sachets, positioning them just so, then stepped back to evaluate, saying "There — that looks fine, dear."

The camisole was next. She had me raise my hands over my head and she gently worked the camisole down over my head and onto my shoulders, being careful not to let the fine fabric touch my makeup, and then drew it over my padded brassiere, giving a final tug or two at the waist.

"Now for your petticoat, mon chéri. Here, sit on the bed."

I sat down, my legs dangling. Mimi moved the vanity chair close to me and sat down. She took the petticoat and gathered it up and guided it over my feet and up to my knees. Wordlessly, I stood and took the waist of the petticoat and gently pulled it the rest of the way.

The poet‘s blouse came next. As with the camisole, she guided the blouse down my raised arms, carefully avoiding my face and makeup. When the blouse was in-place and adjusted, she stepped back and looked me over.

"Such a beautiful blouse, mon chéri — it‘s exquisite" she whispered.


I again sat on the bed as she gathered the skirt, opened the waistband, and guided it over my ankles. It was tricky; she had to gather folds of the petticoat and guide them through the waistband, being careful not to let the delicate material snag on the zipper. After a couple of unsuccessful attempts, she asked me "You dressed in this skirt and petticoat before, right? How in the world did you get into the skirt?"

"With great difficulty, nanny" I replied with a chuckle, adding "I nearly tore my petticoat."

She made one more half-hearted attempt and then, with a smile on her face, she said "I have an idea, mon chéri. You wait right here — I‘ll be back in a minute."

She came back with three of my mother‘s scarves draped around her neck. The scarves were all different colors and patterns, but they all shared one thing in common: they were long narrow rectangular scarves.

"Now lie down on your bed for me, mon chéri" she said with a playful tone. Not knowing what she had in mind, I lay down, my head propped up on the profusion of pillows, my knees bent.

She took a scarf from around her neck and slipped it under my legs, and then drew it out to its full length so that it was perpendicular to my legs. When she was done, she did the same thing with the second scarf, saying "My idea, mon chéri, is that if I tie these scarves around your petticoat, it will make it very easy for me to put on your skirt."

When the three scarves were laid out, she removed all but one of the pillows behind my head and had me lay flat on the bed, straightening out my legs. Then she began to tie the scarves; one just above my knees, one just below them, and one at the petticoat‘s hemline. She tied them tight and I let out a little grunt when she tied the first one.

"Are you alright, mon chéri? They‘re not too tight are they?" she asked.

"No, nanny, they‘re not too tight" I lisped.

When she was done, she stepped back and gave me a long look. "My, my, just look at you" she said, a wry smile on her lips.

She sat down on the bed next to me and brushed a bit of my hair away from my face. "This would be a good time to discuss the Halloween costume party at the Pheasant Run Inn. I think we should go, Evelyn. I have a perfect costume in mind for you — I know just where to get it; there‘s a specialty costume shop in the city where they custom make costumes and other things. We can get an eye mask to wear with it. Nobody would recognize you."

All I could think of was to ask again about the costume she had in mind.

"Oh, you‘ll like it mon chéri" she whispered. "It‘s an Alice in Wonderland party dress… something a young girl might wear… with a really pretty petticoat, much like the one you‘re wearing now, and pettipants too."

"Oh" I titched. I was swept up in the moment, envisioning dressing and going out in a pretty blue or pink party dress with lace and ruffles and a petticoat and pettipants. "Oh my" I lisped, picturing the dress in my mind. "Are you sure I‘ll be alright, nanny?"

"Of course, mon chéri — I wouldn‘t be asking you if I didn‘t think it would be good for you" she whispered, brushing back another strand of my hair. "It‘s all part of making you more confident going out as a girl" she added.

"What color is it?" I asked.

"Why, Alice blue, of course, mon chéri."

"Okay, nanny… if you want, I‘ll go…" I was in no state to refuse.

"Good!" she said with a smile. "I‘ll call them right now. You wait right here while I go fetch their telephone number."

She rose from the bed and left the room, telling me that the flyer with the phone number was in her room. I couldn‘t believe the predicament I was in; there I was, lying in bed, dressed in exquisite and utterly feminine things, my frothy petticoat and silk stocking‘d legs bound by three tightly tied scarves. I took a deep breath and let out a quivering moan, clasping the corners of the pillow behind my head and began to titch rhythmically, laying a still as possible, not wanting to loosen the scarves tied around my legs. My daintie was becoming stimulated, but was not noticeable beneath the petticoat which had bunched up a bit around my pelvis. Mimi took the longest time it seemed, time I spent in bed with my legs bound. It was probably only five minutes, but it seemed like an eternity.

She arrived with the flyer. She fetched the cordless phone on my nightstand, sat down next to me, smiled, and apologized for taking so long. Then she dialed the number and was soon connected to someone at the inn. I lay there as she spoke in the phone, asking about reservations and rooms. It turned out that all the rooms were taken, but there were still reservations available for dinner and the party.

"Wonderful" she said, adding "I‘d like a reservation for two — myself and my…" she looked down at me, smiled, and said "my friend‘s daughter". There was a pause and she added "Yes… she‘s eighteen."

All I could think was that I would, at some point, have to show my identification card which showed that I was a boy.

Mimi patted me on my knee as she read off her credit card information and gave our names: "… yes, that‘s correct, Evelyn Fairechild."

She disconnected and put the phone on the nightstand, saying "All set, dear. Too bad we couldn‘t get a couple of rooms — but they put us on a waiting list."

"Oh Mimi" I sighed. I told her my concerns about showing my identification card and she brushed them off.

"Now, let‘s finish dressing you, Miss Fairechild" she said in a soft French accent. She placed a cylindrical bolster pillow beneath my calves to raise my feet, and then began to fit the skirt over my feet and up to the bolster pillow. She then helped me lift my legs higher and I held them up so that she could work the skirt just past my knees. Except for having to hold my legs up, the operation was easy — the skirt slid easily over the bound petticoat. With her help, I swung my legs over to the side of the bed and stood facing the mirrors. The bottommost scarf fell off the petticoat and onto the floor, but the other two scarves held. She drew the skirt to my waist and we both tucked the blouse in beneath the skirt. The skirt was zipped and the wide satin sash was buckled. Mimi had me hold up the skirt while she undid the two remaining scarves. She was facing away from the mirror as she dealt with the scarves and I had a private moment with myself in the mirror, watching as my well-dressed nanny attended to me, releasing me from my petticoat bindings. Then she took the opportunity to tug at the hems of the blouse and chemise, pulling them down past the taught waist of the skirt.

"Now sit at your dressing table, dear, and let‘s get you finished up" she said gaily, putting her hand on my shoulder and guiding me over to my vanity.


We spent a half-hour or so at the vanity. Mimi drew back my hair in a soft gentle drape and fastened it with a big white chiffon hair bow, adding the white lace scarf to the bow to make long streamers. She fastened the black velvet choker with the black and white cameo around my neck. After I put on the black satin stiletto heel open-toe pumps that Auntie included with the ensemble, Mimi wrapped and clasped one of mother‘s pearl necklaces around my ankle as an ankle bracelet. I wore my pearl dropped earrings and my pearl bracelet over the antique white fingerless crocheted gloves Auntie had sent.

After a final touch-up of my makeup, Mimi and I left my boudoir and descended the staircase to take some photographs. As usual, the setting was our formal parlor and Mimi had me pose by the piano and in our big wingback chair. I took some pictures of her as well. I rarely spoke for my mood was so dreamy, and when I did, my voice was soft and lilting. Mimi sensed just how affected I was by the dressing; she was quiet as well and gently guided my through the rest of the morning. We then began to prepare a light lunch.

"I think after lunch you should take a nap, mon chéri… you look a little tired and you do need your beauty rest" she said.

"Yes, I think I will take a nap, nanny" I replied, leaving out what I would do before napping.


Before we ate, I went back to my boudoir to freshen up and use the toilet. I donned my cashmere daintie glove for my daintie was becoming so creamy I was afraid I‘d soil my panties.

As we ate at our dining table Mimi asked coyly "Would you like me to help you undress for your nap?"

"No… that‘s alright Mimi… I‘d rather do it myself if you don‘t mind" I replied, blushing, looking down to avoid eye contact. I didn‘t want her help because I so wanted to cream while dressed in my exquisite ensemble.

"Of course, dear; I understand" she said reassuringly. "I think I‘ll take a nap as well. Perhaps you could help me out of my dress before you retire?"

"Of course, Mimi."


We finished eating and Mimi told me to go upstairs and wait for her. I turned on the stereo and played some soft music, then sat down at my vanity to touch up my makeup. She arrived in a few minutes, carrying her black marabou-trimmed chiffon robe. She draped the robe across my bed and stood facing the mirrors. She removed her belt then, in a soft voice, asked "Miss Evelyn? Would you unzip me dear?"

I swallowed and stepped behind her and slowly drew down the zipper, expecting to reveal her black lace over white satin foundations that she had modeled for me before, but it I encountered something different — a silver satin camisole and tap pantie with black lace trim. She was wearing a garter belt for I could see its black suspenders appearing from beneath the tap pantie to clasp her black seamed stockings. With the dress unzipped, she held out her arm so that I could help her out of her sleeve. She stepped out of the dress and I held it for her, draped over my arm, wide eyed. The camisole had a button front, trimmed with black lace. She gave a turn and a pose in the mirror, smiling at me and my open mouth gape. "How do I look mon chéri?"

"Oh my goodness, Mimi" I replied breathlessly. "That‘s such a beautiful set" I added with real admiration.

"Why thank you, dear. I just purchased it recently. Its nice being a lady, isn‘t it? You get to wear such lovely underthings. You like wearing nice underthings, don‘t you, Evelyn?"

"Yes, nanny" I replied, blushing.

She took another turn, admiring herself in the mirror, and then donned the robe. She took her dress from my crooked arm and laid it on the wingback chair along with her red belt.

"Well, I think I‘ll go take a little nap as well, mon chéri. Would you mind if I slept in your mommy‘s room? I took the sheets off my bed this morning and they aren‘t laundered yet."

"No Mimi — of course not" I replied.

"Are you sure you don‘t want me to help you undress, dear?" she asked quietly.

I hesitated for a moment. I was in such a creamy mood that I was afraid I wouldn‘t be able to control myself around her if she stayed. "I‘m sorry Mimi — I‘d rather undress in private if you don‘t mind."

"Of course not dear… I understand" she answered kindly. "At least let me turn down your bed for you" she added. Not waiting for a reply, she turned back the bed coverings and smoothed them out, then plumped up a few of the pillows. When finished, she turned to me and said "I‘ll come and wake you in a couple of hours and we‘ll decide what you‘ll wear for dinner. Perhaps I‘ll take a look in your mommy‘s closet for a nice dinner dress for you. Perhaps there‘s something special of hers that you‘d like to wear? You can let me know after your nap."

Then she gave me a wet kiss on the cheek and whispered "Pleasant dreams, Miss Evelyn." And with that, she left the room, closing the door behind her, leaving her dress draped across the wingback chair.


I waited a few moments before locking the door, and then I moved the loveseat from the foot of the bed to the side of the bed to face the mirrors of the dressing screen. I draped the mink throw across the loveseat, and then arranged various pillows on top, putting the feminine heart-shaped boudoir pillow in the middle. Then, for the third time that day, I went to my bathroom and partook, elevating my senses so to better experience the upcoming sensations and pleasures. I poured a glass of sherry from the decanter then sat on the loveseat, striking a fetching pose, and examined my reflection in the mirror, titching, channeling the oh-so-sensual events of the day into the moment.

I couldn‘t believe what Mimi had done to me. She had teased me to the cusp purest sensuality, completely overwhelmed my senses and subjugated me to her whims. I just couldn‘t fathom her intentions. Was this how ladies interacted? Was she simply introducing me to the pleasures of femininity, just helping me feel ’comfortable‘? Or was she intentionally teasing me, knowing that behind the locked door of my boudoir, I would be creaming, my thoughts on her and what she had done to me? Was there a difference? Did it matter? What I did know was I had Mimi‘s unspoken but explicit approval to cream. Ensconced in my boudoir, my whole being vibrantly charged, I began to play amongst my pillows. I thought that the longer I could dally, lingering near the precipice, the deeper my creaming would be, completely purging myself of the awful boy hormones welling inside of me. My dressing of taffeta, tulle, lace, and silk merged with the velvet, silk, lace, and fine linen of my pillows and the mink throw.

Why had Mimi left her dress? It was if she was sitting in the chair, watching me…

Nearly an hour had passed in exquisite pleasure when the moment arrived. I tried to contain my cries, but doubted that Mimi was unaware.


I managed to undress without soiling anything other than my bikini panties which I washed in the sink and hung to dry on a towel rack. I straightened my boudoir, putting the loveseat back and laying my garments on it as I finished undressing, donned couche-culottes and the lilac chiffon peignoir, unlocked the door, then slipped between the fine linen sheets and fell asleep.

It was mid-afternoon when Mimi knocked on the door and entered. She had changed into her claret red ballet dress with a black lace scarf tied loosely around her neck. She was still wearing her black stockings and her red pumps. She brought a tray of cocktail sandwiches and a pot of black tea and set them on the vanity, then sat down on the bed and waited for me to fully wake and sit up. She asked if I had a pleasant nap and inquired whether I was wearing couche-culottes and if they were wet (they weren‘t).

"I have an idea for your dinner dressing" she said. "Let me go fetch it."


I got out of bed and put on the matching robe, then began making my bed. Mimi returned with something I had always wanted to dress in properly, but never had the chance — a stunning black velvet floor-length formal column dress, the silk velvet of the highest quality. This was a dress mother wore to the most formal affairs. Although I had tried it on briefly in the past, I never had the chance to give it the slow and meticulous dressing it deserved. The dress was sleeveless, but had two wide straps that created cap sleeves, made of white duchess satin, attached to the bodice with rhinestone clasps, connecting to a white duchess satin chapel drape in the back with streamers that fell almost to the floor. Along with the gown, Mimi brought black velvet opera length gloves, thirteen buttons on each, that mother wore with the gown. She hung the gown and gloves on the dressing screen then helped me finish making my bed.

"What do you think of my choice, dear?"

"It‘s wonderful, nanny. I‘ve always loved that gown, but I‘ve never had a chance to properly dress in it."

"Well, now‘s your chance" she replied with a wink.


I used the toilet then sat at my vanity, drinking my tea and eating the sandwiches that Mimi had thoughtfully brought. I watched as she selected my underdressing, humming to herself as she did. She said I should wear fresh underthings and chose the shimmering silver gray jacquard with ecru bobbin lace trim camisole and tap pantie. The pettislip would not be needed, she said, because the gown was lined with white satin. For foundations, she chose the rather risqué set of pink satin and shimmering gray lace; full-cup brassiere, a waist cincher, bikini panties, and tulip panties. She finished the under dressing with black French heel silk stockings. She also retrieved short robe that matched the camisole and tap pantie in anticipation that once my under dressing was completed I would don the robe and do a bit of grooming before finishing with the gown.

As she did that morning, she placed the bikini panties and the tulip panties behind the dressing screen along with a fresh pantie napkin, which caused me to blush. The camisole and tap pantie were hung from the dressing screen, and the remaining foundations were draped on the bed.

The next hour or so was spent dressing me, much the same as she had that morning. I went behind the dressing screen and donned the panties and pantie napkin, then stood facing the mirrors as she clothed me in the foundations and the camisole. I slipped into the matching short robe and sat at the vanity to draw on the stockings and the tap pantie. As before, Mimi rolled the stockings for me.

Although I was quite affected by this repeat of the morning‘s dressing, I was a bit more relaxed and light-hearted, not stunned into silence by Mimi‘s actions as I had been that morning. Rather than withdrawing as I had, refusing to admire myself in the mirror unless Mimi wasn‘t looking, I did so now, striking modest admiring poses and postures, primping and preening a bit.

"See — you‘re becoming more comfortable, aren‘t you Evelyn?" she asked, watching me as I did a little turn in the mirror.

"Yes, just a little nanny" I replied, ceasing my posing and withdrawing, as I felt that I was caught doing an illicit thing.

"Now, now; don‘t stop mon chéri. You‘re finally starting to come out of your shell. You‘re like a beautiful butterfly, emerging from her cocoon."

I had to giggle at her metaphor. Not wanting to be rude, I smiled brightly and made another pose, saying "I‘ll try, nanny. I‘m just a little… you know… uncomfortable."

"I know you are — that‘s why I‘m here" she replied.


The time came to dress me in the exquisite velvet gown, and Mimi had me sit on the edge of the bed as she opened the gown and I guided my legs through.

"No need to tie you up in your petticoats with this gown" she remarked, causing me to blush again.

We decided that my hair should be worn up, and I used the bun curler to create a fetching coiffure, Mimi helping me, standing behind me as I sat at the vanity, arranging strands of my hair just so, and suggesting that I let several long strands fall for a more dramatic effect. After I freshened my makeup, Mimi helped me into the velvet gloves and buttoned them for me. She remarked how well the gloves fit and how fortunate I was that my hands, like my feet, were small and daintie like a lady‘s.

"You should wear your mommy‘s diamonds, dear… especially the tiara. She has a hair comb that‘s decorated with rhinestones, doesn‘t she?" Together, Mimi and I went to my mother‘s room where I sat at mother‘s vanity while Mimi decorated me with my mother‘s diamonds, occasionally staring at the photograph of me in the St. John‘s knit. The bracelet looked so dramatic over the black velvet glove. She found the rhinestone decorated comb and fixed my bun with it. With a bit of drama, she placed the diamond tiara on my head, telling me I looked like a princess. When we had walked from my room to mother‘s room, she had noticed that the gown was too long and I had to hold it up. Mimi now looked through mother‘s closet for the highest pair of appropriate heels she could find, telling me they were needed to keep the hem of the gown from dragging. She found a pair of four and a half inch stiletto heel T-strap sandals, the straps seemingly invisible beneath their decorations of rhinestones and an occasional sapphire blue bead. The contrast of the flirty shoes against my sheer black silk stockings was almost gauche, but in keeping with the rest of the ensemble.

Mimi said she wanted to finish the roll of film by photographing me in the gown. "I think you should wear some fur for the pictures" she added.

Back to my boudoir we went. I really had to mince on the high heels. The calves of my legs were becoming sore — my wearing of heels over the past few days was having an effect.

We couldn‘t decide between the white fox stole and the white fox capelet, so we went downstairs with both. My first pose was at the foot of the stairs, holding the stole by its collar at my side, letting it puddle on the floor. Mimi took about a half-dozen photographs, carefully posing me for each one. One was a pose of me all cuddly in the white fox capelet, my diamonds twinkling in the last vestiges of afternoon light.


After the roll of film was finished, we took a half hour or so to review and decide on a digital camera. Together, we sat in the study and I showed her what I had found out. We decided on a top-of-the-line camera and we ordered it, using my mother‘s credit card (Mimi assured me that mother had insisted that the camera be bought using her credit card).

We then had dinner, Mimi preparing a packaged chicken dish as I set the table. We had wine with dinner. Mimi talked about how much fun she had that day, saying she really enjoyed dressing me, and asked me if I had enjoyed it as well.

"Yes, nanny, I did have fun" I replied, then went on to add that I felt embarrassed by some of the more personal and intimate moments ’…when I was scantily clad‘ I offered, blushing as I said so.

"Oh, I know you did, but you shouldn‘t; it doesn‘t bother me in the least, why should it bother you?"

I couldn‘t think of a reply. Mimi continued, saying that she hoped she‘d have more opportunities to dress me. Then she added "And you were able to fit in a nice afternoon nap. I think it‘s important that you have time for a little beauty rest during the day."

I felt flush and my skin tingled as I recalled the tantalizing hour or so I spent near the cusp and wondering if she heard my cries when the moment arrived.

She changed the subject, telling me that she had promised the realtor she worked with to show a house the next day. She would be gone from mid-morning to late afternoon.


After dinner, she left me downstairs while she attended to things upstairs. Soon, she was calling me from the top of the stairs, saying "Come, Evelyn. It‘s time for your nighttime routine."

She had changed into her black lace halter top pantsuit and her black chiffon robe with black marabou trim. She led me to my mother‘s room and undressed me of the diamonds, shoes, gloves and gown. Then it was back to my boudoir where she had put everything away, but left the dressing screen unchanged so that the mirrors faced the bed. She had laid the white silk charmeuse chemise, tap pantie, pajama bottoms, and robe on the bed along with the cotton stockings and satin bustier. I knew what waited for me behind the dressing screen — the couche-culottes.

I donned the short robe and sat at the vanity. Mimi sat on the loveseat, watching me as I removed my stockings, handing them to her. I stood, removed the robe, and Mimi helped me out of the camisole, and then undid my brassiere and waist cincher. Now behind the dressing screen, I donned the couch-culottes and the terrycloth robe that Mimi had laid on the ottoman. She then excused herself to tidy up mother‘s room (we had left the ensemble and jewelry on the bed) while I cleansed my face with cold cream and massaged lotion all over, adding a good sized dollop of lotion to my daintie.


I was applying lotion to my legs when Mimi reentered. A few minutes later, she was dressing me in the bustier, rolling my stockings for me, and helping me into the chemise. I sat on the bed facing the mirrored dressing screen as she opened the tap panties for me to step into, then letting me stand to draw them up over the plastic panties. This was repeated with the pajama bottoms. Finally, she helped me into the robe. After donning my stiletto-heeled boudoir slippers, we went downstairs to watch a little television and to have a cup or two of her tea. We sat on the couch, entertained by a romantic comedy, as we sipped tea and I brushed my hair a hundred strokes. Mimi took over brushing after I neared the mark, slowly guiding the brush through my hair. She then tied my hair with the narrow foot-long length of white silk that was in the pocket of my robe. When done, she kissed me on the cheek and said "Off to bed with you now." It was only nine o‘clock or so. I ascended the stairs to my boudoir.


I parted my robe and snuggled into bed, sitting up and in the soft light of the bedside lamp, taking stock of myself in the dressing mirror. It had been a week since my mother had left and I thought about just how different my holiday was from what I had thought it would be. I had anticipated being left mostly alone, playing dress-up in private whenever the muse struck. But instead, I was completely overwhelmed by Mimi — it was almost suffocating how she had taken total control of my agenda. I hadn‘t worn boy‘s underwear for a week and, in fact, had only dressed in boy‘s outerwear when I was at school. I should be rebelling against Mimi‘s clutches but it seemed impossible; after all, I was the one who decided to dress up in ’something soft and feminine‘ to greet her the previous Sunday. I felt utterly helpless, powerless, and, as Mimi would say, inadequate. And the way she had done it; making me wear couche-culottes and tacitly encouraging me to wet myself, dressing me, photographing me, and going out of her way to dress herself most femininely, unabashedly showing off her foundations and lingerie. Then my thoughts turned to how absolutely splendid the day had been — dressed by my nanny, sent to bed for a splendid afternoon revelry, then dressed again…

Everything became still and silent as a tantalizing tingling sensation came over me. Sometime later, I fell into a blissful dream-filled sleep.


To be continued…

The Awakening of Evelyn - Book 5

Author: 

  • Evelyn D. Fairechild

Audience Rating: 

  • Restricted Audience (r)

Publication: 

  • Novel Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

Other Keywords: 

  • lingerie
  • Petticoats
  • Soft Sweaters
  • Boudoir
  • Nanny

Permission: 

  • Posted by author(s)

The Awakening of Evelyn

Book 5

Evelyn D. Fairechild


The second week of Evelyn's holiday with his nanny unfolds in interesting ways


Chapter Sixteen — The second week of my holiday

Sunday

I awoke fairly early and unlocked my bedroom door, opening it a bit, threw on my robe, and then snuggled back into bed. I heard Mimi rustling around downstairs. I glanced at the bedside clock; she would be leaving in an hour or less.

I was anticipating that Mimi would soon come to wake me and, like the previous mornings, have me drink tea and play our little melodrama; I would tell her I had wet myself, she would check for leakage and in a sympathetic tone, lecture me about my inadequacies. There was no acknowledgement from her that it was just a game, a little intimate theater to further bring me into her clutches, but I was sure nonetheless. The shame of it was that I enjoyed the game, and wondered how far it would go.

My couche-culottes were already damp and an urge to pass water came over me quickly. I was about to rise and use the toilet when I heard Mimi coming up the stairs, so I decided to wait. I was sitting up in bed, wondering what twist Mimi would add to our little game when she gently knocked and entered the room. She was wearing her blue checked robe, loosely tied to reveal her black lace on white satin foundations. She had done her hair and makeup and I surmised that she had come to wake me before she finished dressing, using the opportunity for a bit of intimacy.

"Good morning, dear, did you sleep well?" she asked as she sat on the bed next to me, adding "…and how are you this morning?" She gave me a peck on the cheek.

After saying I slept well, I hesitated for a few moments then added with a whine "Nanny? I wet myself again…"

"It‘s alright, dear. Let‘s check you" she said gently.

I sat up on my knees and she helped me remove my robe. I began to wet myself a bit as I drew down my pajama bottoms, revealing my panties and garter suspenders. As she had done the previous mornings, she fingered the bottom hems of my panties and the garter suspenders for wetness, and began to lecture me.

"Tsk, tsk… you poor dear… I know you feel ashamed about your bedwetting, but really, dear, it‘s to be expected. You‘re so delicate… so frail… just a frail little wisp of a boy… We‘ll just have to deal with it… It‘s a good thing that I had you wear couche-culottes, isn‘t it, dear?"

"Yes nanny" I replied with a lisp as I drew my pajama bottoms up.

"You probably feel so ashamed right now, am I right?" she asked gently.

"Yes nanny" I sniffed. She as gently stroking my back and didn‘t respond to my admission. She was looking at me intently, as if to ask "well?"

Instead of retreating, I let myself be taken in by the melodrama. I sniffed again and sobbed "I‘m just a bedwetting sissy, aren‘t I nanny?"

"There, there, mon chéri — let it out…"

My eyes began to tear up. Some of them were pretend, some of them were real. I shuddered and sobbed and let out a moan, repeating myself "…just a bedwetting sissy… I‘m so ashamed, nanny…"

"Oh, you poor thing…" she whispered, gently stroking my back. "It‘s alright. Go ahead and cry dear — it‘s good for you. It‘s just you and me here… go ahead and cry all you want. You can trust me, dear. I understand… you‘re at such a vulnerable and delicate stage right now, trying to accept yourself as a lady. Tsk, tsk… no need to punish yourself for being a… a bedwetting sissy as you said…" She let her words hang in the air for a moment before continuing "…or… or you could say you‘re a fine and delicate lady. You know what will take your mind off your bedwetting? Dressing up as a pretty girl in a pretty dress and high heels, with pretty intimates and stockings, just like your mommy wants you to do; you‘ll be thinking about how pretty and feminine you are instead of your bedwetting issues. Don‘t you agree, dear? Don‘t you think that you should dress up in a nice pretty dress and high heels and lacy little intimates? Hmm?"

"Yes, nanny" I sobbed.

"Yes, what, dear?" she asked.

With a whimper, I replied "Yes, I should dress up as a lady in high heels and a pretty dress."

"And pretty little intimates, too?" she added, coaxing me along.

"Yes, nanny… and lacy intimates, too."

"Good for you, mon chéri" she said, changing her mildly inquisitorial tone. "So I don‘t have to worry about you while I‘m gone today, do I? You‘ll be dressed up all day, won‘t you?"

"Yes, nanny" I sniffed.

"Now, you need to change out of your wet couche-culottes now, or can you help me make your bed first?" she asked.

I told her I didn‘t have to change and after slipping into my robe, we made the bed. She asked me what I was planning on dressing in that day and I offered that I was thinking about the charcoal gray pleated skirt and the white turtleneck sweater. She said that sounded fine, adding "But I‘d like for you to dress in something a little more elegant for dinner."


It was time for her to get ready to go. She went downstairs to finish dressing as I gathered up a fresh pair of terrycloth panties to change into and brushed my hair. By the time I made it down the stairs and on my way to the laundry room, Mimi had finished dressing, appearing in a black wool suit; pleated skirt and fitted jacket, looking ever so professional. She said her goodbyes, again asking for my reassurance that I‘d be dressing up while she was gone.

"Oh, and one more thing… I thought I‘d drop off the film for developing. Now I know what you‘re thinking, dear, but it will be alright — the place I have in mind is discrete and out-of-the-way … near the house I‘m showing today. There‘s no chance the photographs will fall into the, shall we say, wrong hands?"

With a wet kiss on my cheek, she left, leaving me standing in the hall. As she was closing the door behind her, I let myself go, thoroughly soaking my couche-culottes. I was barely able to remove my pajama bottoms, panties, and stockings without soiling them.


After breakfast, I had a nice long bath, then after applying my lotions, moisturizers, and powder, dressed in the skirt and sweater that I mentioned to Mimi that morning, donning all the proper foundations — the ’lacy little intimates‘ I had promised her I‘d wear. I accessorized with a nice scarf of mother‘s and some of her artisan jewelry. My makeup was hues of plum and brown to match the fall colors of the scarf

I spent a couple of hours finishing my schoolwork. For some reason, I was able to concentrate and get all my studying in, even getting a bit ahead.

I had just finished lunch and thinking about going upstairs for a lovely little nap when mother called. She was in Paris and had time to talk.

She told me she had bought quite a few things in London for me and sent them all off, and that the packages should arrive in another week or so. She had bought some things for Mimi, too, and they were included in the packages. "I hope you like the things I bought for you dear. They‘re really quite nice… the finest cashmere I‘ve ever felt. I got you a beautiful white two-piece set and lots of other things, too, including a couple of adorable pastel tartan skirts."

"Thank you, mommy; I can‘t wait to see them" I cooed.

"And I can‘t wait to see you in them, darling" she replied back.

She said Paris was cold but still beautiful and that she was looking forward to having a day to do some shopping for me. "I‘ve seen boutiques that have some exquisite things…" she said.

The conversation moved onto my dressing-up and how Mimi was helping me. I gave her a broad synopsis of what was going on, leaving out any discussion of couche-culottes and the intimate dressings of the day before, as well as wearing underthings to school. I told her about our aborted foray into Macy‘s and how I just wasn‘t ready. She understood and said not to worry — she was looking forward to giving me some deportment lessons when she came home. In the meantime, I should just get comfortable dressing up around the house and going on drives with Mimi. She would talk to Mimi and make sure she wasn‘t pushing me too far too soon. I told her that Mimi had backed off after the incident and it wouldn‘t be necessary.

She asked about school and the library, and asked me what I was wearing to work. I told her how Mimi had me wear the fawn slacks and sweater and the sweater jacket, but not about changing into a dress later.

"Oh, I‘m glad Mimi had you dress nicely. Did Melanie say anything?"

I thought her question was unusual and inquired "No… not really. Why do you ask?"

"Well, Melanie mentioned to me one day that she thought you were well-suited to be a librarian and that it was too bad you were a boy because almost all librarians were ladies — they didn‘t like having boys around and rarely hired them." She paused for a moment and cleared her throat. "Then she told me that she thought you‘d make for a really cute girl and asked if you ever dressed up as a girl. So I kind of mentioned to her that you might be going through a phase. ’Oh really?‘ she asked, ’what kind of phase?‘ So I told her that, well, you had been wearing dresses recently."

"Mother!" I gasped, "How could you?"

"Don‘t be angry dear. Melanie is quite liberal and open to these sorts of things. She said she thought that was really sweet and that it explained a lot about you. She asked me what I thought about it and I said that I wanted what was best for you and that if you liked dressing up as a girl that was fine with me. I admitted to her I was kind of encouraging you. Then she said ’Well, if he gets to the point where he would like to dress up for work, that‘s okay with me‘ saying that your duties didn‘t require you to interact with anyone who mattered."

I didn‘t know how to reply. Mother‘s observations about Melanie went a long way towards explaining Melanie‘s comments to me at the library — how I was a ’lovely boy‘ and how I was so nicely dressed. Between mother‘s conversation with her and the way I was so sissy-dressed for work, there was little doubt that Melanie knew my secret. It also explained, in part, why mother was always insisting that I ’dress nicely‘ for work. But another part of me was thrilled — maybe I could be the demure and prettily dressed librarian I fancied myself. But another part of me was shocked — how much had my mother really told her? How much had she told her other friends?

"Dear?" she asked, sensing my dilemma over the phone "it‘s alright. I just wanted you to know about Melanie, that‘s all. You know, if it comes up that you‘d like to dress up for work, I bet Melanie wouldn‘t mind at all. You could just ask her, you know."

"Well, I‘ll think about it mommy. I just don‘t want to get caught, you know."

"I know dear. That‘s why I‘m looking forward to moving up to the Hamptons."

I let her last comment just hang there. She sensed that I was completely distracted and began to say her goodbyes. A minute later we hung up.


It was all just too much — my admission to Mimi that morning that I was a bedwetting sissy — and her agreement, the intimate nature of the day before, my mother sending me dresses, and the possibility of dressing up for work — I just had to go upstairs and clear my thoughts, relieve my tensions… purge myself of the awful boy hormones that made me doubt my place in life.

I poured a glass of wine and minced on my heels up to my boudoir. Mimi wasn‘t due back for several hours. An hour later or so, I stood before the mirrors, all done up. My foundations were the white crepe de chine set with white silk stockings and several pairs of panties, well protected by my cashmere daintie glove and a scarf. Over these delicates I wore the crepe-de-chine chemise and dance pantie and my two petticoats; the princess petticoat that Auntie had sent and the white petticoat with the double layer of tulle lace netting that went with the midnight blue gown that mother bought me. I topped it all with the white fox stole, the fingerless crotched gloves, and delicate scarves. I fancied myself as a little girl playing dress-up with her mommy‘s things. My morning ensemble was scattered all about my boudoir. Several pillows were arranged in the center of the bed, waiting for me, along with a hand mirror.

Lifting my petticoats, I nestled onto pillows and had an absolutely scrumptious time, lost in a soft and delicate world. Holding the hand mirror I stared into my eyes, my thoughts were caught up in the conversation I had with my nanny that morning, admitting I was a bedwetting sissy as she gently stroked my back and I wet myself. The moment arrived and I cried out loudly. Still lying on the pillow, influenced by the wine, I drifted off to a blissful sleep.

I awoke when I realized Mimi was opening the door to my boudoir. I had forgotten to lock it — the house had been empty and I was alone, so I just didn‘t think about it. My heart skipped a beat or two then started pounding in my chest. I was caught in a very compromising position; tummy down on the bed, lying on the pillow between my legs, dressed in layers of petticoats and panties. It was obvious what I had been doing. Perhaps she wouldn‘t notice the pillow, I thought — the voluminous petticoats draped over my derriá¨re, hiding the pillow. I had lifted the petticoats in front in order to present my panties to the pillow, and I was laying on their spread of lace, tulle, and organza. It must have been quite a sight, but I didn‘t dare rise or turn over in the slightest for doing so would reveal the pillow and my panties. All I could do was lay still as she entered and sat on the bed, moving the hand mirror aside and putting her hand gently on my back.

"I‘m sorry mon chéri —I didn‘t mean to disturb you. I got done early and I just came back and wanted to check on you. Did I wake you?"

I cleared my throat and replied that she had, but that was alright.

"Did you have a nice nap?" she asked sweetly.

"Uh-huh" I whispered.

"I see that you‘ve been playing dress-up. Good for you. Did you have fun?"

"Yes, nanny" I replied, still not moving, wishing she would go away so I could remove myself from the pillow in private.

"Did you wet yourself?" she asked in a soothing dulcet voice and, without waiting for a reply, added "I should check…" She began to lift the petticoats to expose my panties.

"No, nanny… I‘m fine… really!" I blurted out, not wanting her to see my position on the pillow. But she ignored me, slowly lifting the petticoats off my derriá¨re, completely exposing my embarrassing position on the pillow.

"Nanny… please…" I whispered.

She began to finger the hems of my panties. Perhaps that would be the end of it I thought, but she drew the panties up and to the side and said with concern "Evelyn… you‘re not wearing your couche-culottes."

"I know… I‘m sorry… I just sort of…" I couldn‘t think of a way to end the sentence.

"Well…" she said gently. "I suppose I could let you slide this once. Are you sure you‘re not wet? Is your pillow wet? Hmm?"

"Noooo…" I whined, struck that she had mentioned the pillow.

"Alright then; why don‘t I go fix us some tea and bring you a cup? We‘ll have dinner in a few hours. That will give you plenty of time to dress up nicely for dinner. After all, it‘s been a week since you‘ve come out — you should wear something special." She leaned over and kissed the crown of my head, then patted my pantied derriá¨re.


By the time she reappeared with tea, I had tidied the boudoir and made myself more presentable. I had disrobed down to my chemise and dance panties and donned the matching long robe. I had removed the cashmere glove and scarf from beneath my panties.

Mimi had taken off her black wool suit and donned her blue check robe she had worn that morning, loosely tied as always so that her foundations showed. I sat at the vanity brushing my hair as she gathered up things that need laundering. I told her about mother‘s phone call, leaving out the part about mother‘s conversation with Melanie. A minute or two later, she was sitting on the tuffet behind me, having taken the hair brush from my hand and brushing my hair. Neither of us spoke for a while.

"So tell me about the rest of your day, mon chéri. You had a nice nap, no? A nice nap in bed with your pillows?" she asked coyly.

My face reddened. "Uh… yes, nanny…" I offered.

"Good. You need your little afternoon beauty rests, don‘t you, snuggling up with your pillows?"

I was afraid of where she was going with her questions. It was just too intimate and personal. What did she want me to say? So I mumbled something in response.

"From now on, I‘ll try to make sure that there‘s time for you to have a nice afternoon nap, dear" she said, nearly whispering, adding "…a little beauty nap for my blossoming little lady."

"Uh… okay. Thank you nanny" I breathed. Then, for the sake of propriety, I added "I don‘t need one every day, you know… I mean there days where there might not be time and stuff."

"Of course, but that doesn‘t mean we shouldn‘t try to fit in your nap."

I didn‘t reply and she continued brushing my hair.

"You got a chance to dress up in some special things this afternoon, didn‘t you? Like your pretty petticoats — they‘re special, aren‘t they?" Her voice was so quiet, so mesmerizing; I didn‘t know what to say. I think I replied with a barely audible ’uh-huh".

"You know, you never had a chance to play dress-up like little girls do. You know — little girls go through a stage where they love to dress up in their mommies‘ frilliest and laciest things… You never had the chance to do that… What a shame. So you‘re just making up for that, making up for lost time. That Halloween costume I have in mind for you is really frilly and lacy — I think you‘re going to really enjoy it. And don‘t think you need to dress as an elegant and tasteful young lady around the house all the time — you can dress all frou-frou instead if you like. Would you like that, mon chéri?"

"Yes" I whispered.

"Maybe we should have a special day for you, a frou-frou day, no?"

"Yes, nanny… I‘d like that" I breathed.

"And then I‘ll make sure you have your beauty rest, too" she added.


She gathered up some laundry and was about to leave when she said "That reminds me — I need to take your measurements for the costume." Fifteen minutes later, she had measured me and wrote down the numbers. My waist was twenty-four inches and my chest was twenty-seven without a brassiere, thirty and a half with. My hips were twenty-eight inches.

She left my boudoir to let me chose my own dinner dressing. An hour or so later, I descended the staircase in the pink chiffon dress mother had bought me. I wore something else, too, something I had been thinking about trying; an oh-so-pretty long pink satin peplum waist combing jacket of my mother‘s, fancifully embroidered with vines of lilac, with long full sleeves finished at the cuffs with four inches of pleated chiffon, wide chiffon lapels, and a hidden button closure. It was a little over-the-top, but the combination really seemed to work, especially when I tucked an antique white lace scarf behind the lapels of the combing jacket, I accessorized with the pink and cream two-toned pumps, the pink chiffon hair bow with its cluster of ivory organza flowers and ribbon streamers, and the pearls.

Mimi had dressed up as well, wearing her silver blue chiffon palazzo slacks, beaded blue bustier, and sweeping silver blue embroidered chiffon jacket — one of the mother-of-the-bride ensembles she had modeled. She liked my dinner dressing and agreed that the combing jacket was a nice touch, telling me that I had such elegant taste. "That‘s such a lovely jacket, Evelyn. Perhaps I‘ll set it aside for your frou-frou day, along with your petticoats" she said with a wink as I took a few turns at her request.


During dinner, Mimi said she had dropped off the film and that we could pick it up tomorrow after school. "I‘d like for you to come with me, and you should be dressed, of course."

After dinner, I spent an hour or so in front of the television ironing my freshly laundered underthings, Mimi checking on my progress and technique occasionally.

The evening ended with Mimi undressing me, laying out the blush peach negligee and bed jacket, and making sure that I donned the couche-culottes with pink plastic panties. She left and instructed me to apply my moisturizers and lotions. I was a little tired, and fell asleep before I could do much mischief.


Monday

I awoke early, anticipating my return to school. I had kept my couche-culottes dry throughout the night. I hadn‘t creamed the evening before, and was in the mood, but there really wasn‘t time to properly indulge. I showered and scrubbed, removing the last of the telltale signs and vestiges of makeup and fingernail polish from the last five days. I think Mimi was a little disappointed that she didn‘t get to play our little melodrama that morning.


I had mixed feelings about returning to school. On the one hand, it would be good to see some of my classmates, to get away from Mimi and her smothering and cosseting for a few hours at least. On the other hand, my life had been exorbitantly changed, and I could not reveal any of it to my classmates.

After breakfast, Mimi had me dress in black corduroy slacks, a gray lambswool crew neck sweater, and my gray zip-up sweatshirt. Beneath it all, I wore the silk charmeuse brassiere, garter belt, thong, and bikini panties, as well as dark stockings and another pair of tulip panties.

Mimi dropped me off and I saw Ms. Hunter walking towards me, heading towards our class. She greeted me and we walked together. "I came by your house — did you get the class notes?" she asked.

"Yes" I told her and made up an excuse that I must have been in the shower or something.


During class, I had to consciously remind myself to not be so ladylike in my mannerisms, like sitting in my chair with my legs crossed or fondling my hair. I made it through another distracting school day, aware of my intimate underthings, realizing that my fingernails were too long and manicured for a boy, thinking about what waited for me at home, and feeling numb thinking about the embarrassing position Mimi found me in and the things she said about my ’beauty rest‘.

Mimi picked me up on schedule, and reminded me that we were going to pick up the photographs.

Back home, we had lunch and Mimi sent me off to my boudoir to change. She had obviously spent some time laying out my ensemble. She had selected the St. John‘s knit with the pink silk and cashmere top, accessorized with the coordinated scarf, the pink and gray clutch purse and the matching two-toned pumps, and white silk stockings. Foundations were the set of pink satin and shimmering gray lace, and daywear was the muted lingerie pink with ivory Venetian point lace trim set — camisole, pettislip, and dance panties. On the vanity was the open jewelry case containing the pearls that mother had given me, along with a hair barrette of my mother‘s decorated with organza and tulle flowers in shades of pink and ivory that matched the ensemble. As a final touch, the short robe that matched the pink and gray lace foundations was hung on the back of the slipper chair. How thoughtful of Mimi; I would don the foundations then sit at the vanity, put on the short robe, and do my makeup.

An hour or so later, I descended the staircase. I had added mother‘s gold drop-chain belt that she had dressed me in. Mimi was waiting. "You look absolutely adorable — so very, very pretty" she said with a smile.

My heart was pounding as we exited the house and went to her car. I managed to get situated without tugging my skirt. I slouched down in the seat as Mimi started the car and we drove off. When we were a mile from the house, she patted me on the knee and said with a bit of a giggle "You can sit up now, dear. Let the world see what a pretty young lady you‘ve become."

We drove for about twenty minutes. As Mimi had promised, the drugstore where she had taken her film was out of our normal territory, minimizing the likelihood that anyone would recognize me, either in the photographs or as I sat in the car. Mimi took longer than I expected, so I entertained myself by doing my makeup. She finally arrived carrying a couple of bags — she had purchased several picture frames and a couple of beauty and glamour magazines for me. She said she‘d bought the picture frames to display the best photographs. I asked to see the photographs, but she said "no peeking — you have to wait until we get home."

We drove back by a different route, one that would take us through town, and I protested.

"It‘s shorter dear. Don‘t worry; nobody is going to recognize you."

We drove by ’An Affair to Remember‘, the shop where mother bought me the pink chiffon. It was no longer in the window — and then I remembered; it was hanging in my closet!

As we drove through town, we hit a red light. On the sidewalk were a couple of classmates. They didn‘t see me. At another red light, though, I looked over at the car beside us and recognized Ms. Hunter. I immediately turned towards Mimi and whispered, in a panic, "That‘s my English teacher. I can‘t let her see me!" My voice was trembling and I‘m sure my face turned white.

"It‘s alright, dear" she said calmly, glancing behind me. "She‘s not even looking this way."

We arrived home and once inside, I was exhilarated. I had gone out again as a girl! Not just as a girl, but as a girl in a very classy ensemble, all turned out, wearing very fine lingerie, expensive pearls, and high heels.


We sat on the couch and went through the photographs. Mimi was an excellent photographer — the pictures were so much better than the snapshots mother had taken. I was really stunned and affected by what I saw; it was hard to believe that the oh-so-pretty and exquisitely dressed young lady in the photographs was me. There she was, dressed in a two-piece chiffon tea dressing; pink and red roses and lilacs against an ivory background, flirty stiletto heeled T-strap sandals on her shapely ankles, a matching scarf tied around her neck, sitting in a chair with a schoolbook, looking studious and demure. And who was this fetching young vision in that feminine pink chiffon dress and pink heels, standing by the piano, the lighting perfect, modeling a white fur capelet and a mink and sable coat? She was so enticing. And who was this breathtaking young lady sitting in a big wingback chair in a to-die-for poet‘s blouse and taffeta skirt, her petticoat showing, wearing fingerless gloves that showed her manicured and polished nails, a black velvet choker around her thin alabaster white neck? She was obviously sophisticated and cultured, well-bred and cared for. And there she was again, standing by a grand piano, exuding class and grace, a big white chiffon hair bow with long lace streamers now visible, adding another level of pure femininity. Then — oh my — who was this young starlet in a black velvet gown with a white satin cathedral train draped down her back, a diamond bracelet flashing against the black velvet opera gloves, a diamond tiara on her swept up hair, and high, high heels decorated with sparkling rhinestones? Oh, what class, what a cupcake. And her pose! Standing seductively at the foot of our stairs, holding a white fox stole, casually letting it puddle on the carpet?

Mimi was sitting close to me while we viewed the photographs, commenting on them, telling me how lovely I was, evaluating elements of my dressing, and saying things like "See? How could anyone think you were anything but a very pretty young lady? You just refuse to believe how pretty you are and easily you could live as a girl…"

There was a set of photos of Mimi as well, stunningly dressed in her black lace dress, a wide shiny red belt, a red satin choker, and a riotous coif, ready for a night on the town. One of Mimi‘s comments was "Oh look, there‘s her nanny…"

We selected six of the photographs to put into the frames. Mimi wanted to have two of the photographs — one of me in the poets blouse and taffeta skirt and one in the black velvet — enlarged and printed on high-quality paper. We put one of the photographs of Mimi in a frame which ended up in my boudoir. The remaining photographs were placed about the house, one on the grand piano, two in my boudoir, and two replaced old photographs of me on our credenza and mantelpiece.


I had a bit of reading to do for school and Mimi sent me to our study. I had a bit of wine during and after dinner. I had a bit too much; by the time I had done my evening routine and dressed in the silk moonglow pajamas, nightshirt, tap pantie, and the requisite couche-culottes, I was a bit tipsy. Mimi tucked me into bed. She was wearing her peach delustered satin halter-topped nightgown and robe. She was really leaning over me as she tucked me in, keeping her breasts close to my face. For the first time, I noticed the nipples of her breasts outlined by the satin and white lace of her nightgown. I couldn‘t help it; they were so close to me. My feelings were very confused about this — I felt that Mimi had purposely leaned over to show her breasts to me. Her nipples must have been stimulated — I had heard that women‘s nipples became hard when stimulated, and that was why they were so well defined beneath her nightgown. These thoughts were on my mind as I drifted off to sleep, helped by the wine.


Tuesday

Mimi came to my room with a cup of tea and set it on the nightstand, still wearing her peach nightgown and robe. She left a few moments later, promising to return in a minute or so. I sat up and sipped the tea. I had a bit of a headache from the wine the night before. A few sips of tea triggered my need to pass water. My couche-culottes were dry, but I was sure that Mimi wanted to have one of our little melodramatic discussions about my bedwetting, given the timing of her visit and the cup of tea, which she knew would have a diuretic effect on me.

I sat up in bed and began to wet myself, a weak stream that would continue for quite a while. Mimi came back and sat on my bed.

"Did you sleep well last night, dear?"

"Oh yes, nanny…" I began, and, after a few pleasantries, I began acting out my part in our little game. I bowed my head, sniffed, and whined "…but… but I wet myself again, nanny. Oh, nanny, I‘m so ashamed. Ever since mommy left and I started wearing ladies clothes, I‘ve been bedwetting."

She adjusted her position on the bed, put her arm around me, and drew me to her breasts. She stroked my hair and whispered in her accent "There, there, mon chéri, it‘s alright. I know, my lovely, I know… You‘re going through such a difficult time. Don‘t worry… it‘s our little secret. No one needs to know about your bedwetting."

Her breasts smelled nice — she must have dabbed on some perfume. This was a new scene in our little play and I was quite taken by it; my nanny taking me to her breasts and petting me as I dampened my couche-culottes.

"Would you like me to check your couche-culottes?" she whispered, adding "I think I should."

"Yes… please, nanny. I don‘t want to wet my things."

"Of course not, dear, of course not."

She released me and I sat up on my knees and drew down my pajama bottoms. She examined my panties and garter suspenders.

"I‘m not sure, mon chéri… but I think you might have wet your things" she said in a concerned manner.

"Oh no, nanny… are you sure?" I whined.

"Draw down your panties, dear, and let me check further."

Down went my silk tap panties, revealing the nylon over plastic briefs.

"Lean over a bit, dear, so I can check…" she said gently. I leaned over, resting on my elbows, my derriá¨re elevated. I was still passing a weak stream of water but when I leaned over, my position allowed my stream to increase. She placed her hand on the back of the panties and pinched together a bit of the pantie briefs and the terrycloth panties beneath.

"Hmm… you are wet, aren‘t you, dear?"

"Am I nanny? Am I too wet?" I whined.

"One more little test…" she whispered. Her hand moved between my legs to where the absorbent wicking pad was located and clasped the pad to judge its weight. A shiver of pleasure went through me — did she have any idea what she was doing to me? I let out a little gasp followed by "Ohh…" She slowly withdrew her hand and placed it on my raised derriá¨re and gently patted and rubbed it. I let out another little gasp as I kept passing water.

"Tsk, tsk… you really wet yourself, didn‘t you? It‘s a good thing we checked you when we did; otherwise you would have wet your pretty things. We can‘t have that now, can we?"

"No nanny. What can we do? I‘m so embarrassed, nanny. Please don‘t tell anyone that I wet myself."

"Don‘t worry, dear. It‘s our little secret. No one needs to know that you‘re a bed-wetter. I‘ll take care of you. I think I should get you some different couche-culottes to wear, ones that will hold more and protect your things, okay?"

I had no idea what she had in mind, but I readily agreed, saying "Yes nanny. I think I need that."

"Let‘s take off your things and get you downstairs before you have an accident and wet your things" she said, taking off my pajama bottoms, guiding them past my knees as I lifted them, then doing the same with my tap panties. Then she unclasped my stockings and drew them off, commenting on how shapely my legs were and how the nightly application of lotion was having an effect. During all of this, I was kneeling, my knees and elbows on the bed and my derriá¨re elevated, passing an occasional weak stream of water, trying not to moan for the whole episode had a very erotic affect on me. This was a new level of intimacy between my nanny and me.

I carefully got out of bed. Mimi handed me my soft ribbed cotton pantie briefs, pajama bottoms, camisole, and slate blue cashmere and silk robe. "Go downstairs now, dear, and take care of your couche-culottes and things. I‘ll be down in a minute." Like the evening before, I noticed her nipples outlined by the fabric of her nightgown -- maybe she was affected as well?


An hour and a half later, I was ready for school. It was cold outside, and I wore a pair of brown corduroy slacks, my earth-tone brown Donegal knit crew neck sweater, and my navy blue wool pea coat. Beneath it all was my blue silk surah and white lace foundations, camisole, and tap panties, matched with black stockings. Mimi had selected these things while I took a shower; when I came out to dress, the underthings were neatly placed on the ottoman with a damask pantie napkin on top.

Mimi‘s final words before dropping me off at school were "Don‘t forget — you‘ll be dressing nicely for work today."


I don‘t know how I made it through my two classes. The morning‘s episode kept going through my mind as I sat in class. I became aroused just thinking about it and I‘d catch myself, snap back to reality, and then drift off again. I was getting rather creamy — my slight hangover and the fact that I hadn‘t creamed for over a day was keeping my pantie napkin moist. I wondered about Mimi and me — the fact that her nipples had become hard — was she aroused as well? And how she had shown me her breasts the evening before, and snuggled my head on them that morning — what exactly were her intentions? I couldn‘t fathom intimate contact between us, anything remotely romantic. She was older than my mother! She was almost family! Sure, she was attractive, but, but… But what did I know? I was a complete virgin; I‘d never even kissed a girl. Confusion was an understatement.


Mimi arrived on schedule to pick me up. She had changed her clothes; she was dressed in her white lace-band collar blouse, long black rayon skirt with attached self-tie waist sash, and a black wool swing coat. I had to compliment her — she looked marvelous.

"Your mommy called today. We had a nice chat. I was so good to talk to her" she said as we drove away. "I said you were starting to come out of your shell and just beginning to accept yourself as a lady."

’Just starting?‘ I thought to myself. The last week had been beyond anything I could have imagined — things were moving so quickly.

"She‘s really happy that you are. She wants me to ’keep moving you in the right direction‘ she said, and to do whatever I felt was needed."

I wondered what mother would think about some of the things Mimi was doing with me. I couldn‘t think of a reply. A moment later she said "Oh, and by the way, we chatted a bit about Melanie. She‘s really a nice, accepting person, don‘t you think? Both your mommy and I think that being a librarian really suits you… Miss Evelyn the librarian."

I felt numb, wondering what was in store for me when I got home.


I had a quick lunch — eating was difficult given the butterflies in my stomach. Just as docile as could be, I followed her upstairs to my boudoir. The side-buttoned charcoal gray wool and silk Armani slacks hung from the dressing screen. On the loveseat were the off-white mohair, angora, and merino wool turtleneck and the dove gray alpaca surplice wrap cardigan. On the floor were the black velvet Sabrina heeled pumps. Laid out on my bed were the pewter gray satin brassiere and waspie, the shimmering silver gray jacquard a ecru bobbin lace trimmed camisole and tap pantie, and a pair of black French heel silk stockings. Draped over the back of the slipper chair, borrowed from my mother, was a long beige silk scarf with a cream colored checked pattern. On the vanity top were my antique silver filigree hair clip, a pair of silver strand earrings of mother‘s, and a silver scarf clip. Draped over the wingback chair was mother‘s three quarter length black wool shawl collar coat with self-tie belt, a pair of deep burgundy kid leather gloves, and a big deep burgundy leather shoulder bag, large enough to be used as a book bag.

"Mimi... Eww…" I whined upon taking in the ensemble. The sweaters were the same as I had worn for Mimi that first day, the soft and feminine signal that I wanted her to help me become a lady. But the slacks were even more feminine than the ones I wore that day! And black velvet pumps! How could she? Was she expecting me to wear the scarf too?

"Now, now, Evelyn; we want our lovely librarian to dress appropriately" she answered. "Please don‘t make a fuss."

"But Mimi — what about Melanie?" I lisped.

"Oh, I think she‘ll be most understanding. From what your mommy told me, she already knows you like dressing up. Don‘t you think it‘s time you showed her? Really, Evelyn, I was thinking I should have you wear a dress, so you should consider yourself lucky that I settled on these things."

I fussed a bit more — pointing out that someone else I knew might show up — a classmate or something. We made a compromise; Mimi would allow me to take the argyle sweater that matched the slacks, and I could change into them in case someone did show up.

I acquiesced — what else could I do? Maybe everything would be alright. Within a few minutes, my mood was back to where it was that morning — all creamy and dreamy. I went from fussing with Mimi to being her docile little pet.

She watched me undress from my school clothes, taking them from me and casually tossing them into my ’other‘ room. I removed my stockings and camisole and let Mimi unclasp my brassiere and garter belt. She then sent me behind the dressing screen where she had laid out a pair of white silk panties, a damask pantie napkin, and the shaping pantie on the ottoman. The garter clasps were removed from the shaping pantie — I‘d use the waspie to hold up my stockings. When I came out from behind the screen she had me dust myself with body powder, then stood me in front of the mirror and began dressing me. She wrapped the waspie around my waist and fastened the hooks. The combination of the shaping pantie and the waspie gave me a nice hourglass shape, she said. The brassier was next, followed by the tap pantie, which she held open for me to step into. I had expected her to let me draw the pantie up, but to my surprise, she drew it up instead, whispering "It‘s okay… let me, mon chéri - since you‘re wearing a girdle." The camisole followed — I held my hands over my head and she guided it down. Then I sat on the slipper chair and as she rolled my stockings and handed them to me. After unrolling the stockings up my leg, I stood and held the stocking up while she clasped them to the garter suspenders.

The slacks were next, followed by the turtleneck, the waist worn outside the slacks. The lightweight fabric of the turtleneck wasn‘t enough to obscure the camisole beneath. The cups of the brassiere formed a discernable little bump. But the surplice wrap cardigan hid my underthings from view. I was glad to see that the long billowy slacks mostly covered the black velvet pumps. The scarf and scarf clip was followed with the earrings. Mimi gently gathered stands of hair from my temple and clasped them back with the hair barrette, leaving a few locks of hair to cover the silver strand earrings. She convinced me to put on a bit of neutral lip gloss and a hint of powder — it would protect my lips and skin against the cold dry air, she said.

The dressing went quickly and before I knew it, we were adding things to the big shoulder bag; my sachets, makeup, and the argyle sweater that Mimi let me take in case of an emergency. Just before leaving the room, Mimi went to my closet and retrieved the pleated skirt that matched my slacks and the pettislip that matched my camisole and tap pantie.

"Just in case you have a chance to change" said Mimi, carrying the two hangers holding the garments.

Then I was outside, walking Mimi‘s car, mother‘s long black wool coat tied around me, kid leather gloves on my hands, the bag over my shoulder. As I walked to the car, a little unsteady in my heels, I relished the feel of the full legs of the slacks sliding past my silk stockings, knowing that the movement of the exquisite fabric was a delight to the eye. Mimi draped the skirt and pettislip across the back seat.


Our arrival at the library was inauspicious. Mimi came in with me and Melanie appeared a minute later, coming out of her office escorting one of the docents to the door. She was nicely dressed in a blue patchwork two-piece that complemented her silver hair. She was glad to see Mimi and invited us for coffee. We followed into her office, the sound of my heels clicking on the hardwood floor wear heard clearly over Mimi‘s heels and Melanie‘s flat heels.

"Cold outside, isn‘t it?" Melanie offered. "You can put your coats on the rack" she said, motioning to the coat rack in the corner where her own coat was hung. I removed my gloves while Mimi took off and hung her coat.

"Let me help you dear" said Mimi as I fumbled with the self-tie belt of my mother‘s coat.

’This is it‘ I thought, my mind racing — I was facing Melanie as she sat in her comfortable stuffed chair; Mimi was behind me, ready to help me out of my coat. I felt a little faint and exhaled as the coat came off, revealing my oh-so-soft dressing to Melanie. Her eyes followed me as Mimi and I poured our coffee and sat down on the couch. She smiled broadly and said "My, but just look at you — you‘re dressed very nicely today, dear."

"Thank you, Melanie" I replied, my voice soft, my head bowed.

"I love that sweater — so soft and pretty. What kind of wool is it, dear?"

"I believe its alpaca" I replied.

"Well, it‘s lovely dear. And that‘s a beautiful scarf — it goes so nicely with your sweaters" she added. "And that‘s a pretty skirt and blouse you‘re wearing, Mimi. You two make quite a pair."

Mimi patted me on the knee and replied "Why thank you, Melanie. I‘m trying to be supportive of Evelyn — excuse me — that‘s his middle name — did you know? I prefer to use ’Evelyn‘ when he dresses up. I understand that Ellen told you that Evelyn is going through a phase, no?"

"Yes, she mentioned something" she replied, her voice earnest, waiting for a reply with interest.

"Well" continued Mimi "…you see, Evelyn has always been attracted to dressing up in ladies clothes, and seems so much happier when he‘s all dressed up as a lady… aren‘t you dear?" she said, turning to me and stroking my hair. I didn‘t answer for a moment, so Mimi added "Hmm? Don‘t you dear?"

"Yes" I sighed.

"How sweet" said Melanie. My mind did a tumble — was she going to accept me? "I always thought you‘d make a pretty girl, Evelyn," she continued "and that maybe you should try being a girl. Someone as gentle and sensitive and artistic as you shouldn‘t have to go through life trying to be something you aren‘t. Besides, I‘ve become to think of you as a girl and there‘s no reason you shouldn‘t dress as one."

A wave of relief swept over me — Melanie understood and seemed to be supportive. "Thank you, Melanie… thank you so much for understanding" I replied, looking up for the first time. She was sitting with her chin in her hand, her elbow on her knee, examining me, and giving me her full attention.

"So while Ellen is away," continued Mimi after a moment "I‘ve been encouraging him to come out. In fact, you‘ve dressed up every day since your mother left, haven‘t you Ellen?"

"Yes" I replied bashfully, bowing my head again.

"Really?" Melanie asked.

"Oh yes" Mimi replied, "as soon as he‘s home from school, its straight upstairs and out of his schoolboy clothes and into a nice dress and stockings and heels and makeup and jewelry…"

"Oh, my" Melanie interjected, as if this was pleasing to hear, while I let out a moan of embarrassment.

"Yes" continued Mimi. "She… he… whatever… She dresses so very meticulously and tastefully. She‘s quite beautiful, Melanie. You should see her sometime."

"I‘d like that" she offered, then a moment later said "You know, next week is Halloween week — maybe you should wear a costume next week, Evelyn; dress up as a proper librarian. Would you like to do that, dear?"

I was ecstatic that she thought of the very thing I wanted. "Oh yes, Melanie. You wouldn‘t mind?" I asked hopefully.

"Not at all dear — it‘s up to you."

"What a great idea" Mimi interjected. "You‘ve got several dressings you can draw upon, Evelyn."

Melanie seemed pleased to hear this, adding "It will be nice to have a girl working with me."

"Oh, this is wonderful news, Melanie" Mimi said. "It‘s important that Evelyn gets out more." She paused for a moment then asked "You know that Ellen is moving to the Hamptons?"

"Yes — and I‘ll miss her — and you, too, Evelyn" replied Melanie.

"Well, we‘re thinking that she‘ll want be a full-time girl once she does— we‘ll see."

This was news to me! I let out a little ’oh?‘ I didn‘t know whether Mimi was saying this because it was true, or as a justification for what she said next.

"So while she‘s here, we just want her to become more comfortable going out as a girl. But we do have to take some precautions — Evelyn doesn‘t want everyone to know, especially her classmates and such."

"That‘s understandable" replied Melanie. "I‘m glad you trusted me, Evelyn. And, I guess, this is a perfect place to practice — I doubt you‘ll see any of your classmates here" she chuckled. Then, as an afterthought, she added "Too bad you didn‘t bring a dress today. But I daresay, you‘re so ladylike in your sweaters, slacks, and heels."

Mimi smiled and said "Oh — but Evelyn, your skirt is in the car, remember?"

Melanie smiled broadly and said "Would you like to go get it and put it on, dear?"

I looked at Mimi and then Melanie. Everything in their expressions said I should. Mimi handed me her keys.

"Yes… yes I would" I replied, smiling for the first time. "Thank you so much, Melanie. I‘ll be back in a minute."


I rose and put on my coat and went to the car, heels clicking and reverberating in the empty library. Trancelike, I retrieved the skirt and pettislip from Mimi‘s car and returned to Melanie‘s office.

Mimi and Melanie were laughing about something when I came back in. Melanie suggested I change in the downstairs bathroom — it was large and had a chair. I removed my coat, took my bag, and left. Mimi called behind me "Don‘t forget to add a little padding, dear."

A few minutes later, I had changed into the pettislip and skirt, padded my brassiere, and made up my face. I put the slacks and the argyle sweater on the hangers and hung them on the coat rack as I entered Melanie‘s office.

Melanie‘s reaction was wonderful: "Oh… my… goodness, Evelyn; just look at you sweetheart! You are… are so so pretty!" she exclaimed, her broad smile dimpling her pleasant round face, her eyes bright.


The next couple of hours were wonderful. After a minute or so of effusive compliments on my appearance and ’natural feminine grace‘, all pretense disappeared and I was just Miss Evelyn, the pretty assistant librarian. We chatted as we finished our coffee, and then Mimi left, saying she had errands to run.

Just after Mimi left, Melanie went over a ’just in case scenario‘ as she described it. She and Mimi had talked about it, she said — I took my slacks and sweater up to my office on the third floor and returned downstairs. In case anyone I knew came in, I could go upstairs and change into the slacks and sweater. Melanie then had me help her put up some Halloween decorations and do some filing and re-shelving. I was absolutely delighted that someone besides Mimi knew my secret and accepted me. Melanie was fun to be with and for the first time since mother left, I felt free of Mimi‘s clutches. My feeling of independence and acceptance was cathartic — it felt so wonderful. Melanie was quick to realize my feelings and said that I seemed happy for the first time since she met me.


It was around half past three o‘clock when we heard a car pull up outside. Melanie looked and saw that it was one of the docents escorting an older lady. She said she doubted I knew either of them. Rather than dealing with introductions, I went upstairs to do some shelving.

A half an hour or so later, Melanie called me on the intercom. I was expecting her to tell me the visitors had left, but instead she said calmly "Evelyn — I‘m in my office — I think one of your teachers is here — that one I met at the concert. She‘s looking for a particular book from our new collection. I‘ll be sending her upstairs in a minute."

My heart stopped for a moment. I said something and hung up the phone; so much for my wonderful afternoon as Miss Evelyn.

Into the bathroom I went, hurriedly taking off my heels, skirt, pettislip, scarf, sweater set, brassiere, earrings, and hair clip, then washing the makeup off my face. I heard footsteps coming up the stairwell. I quickly donned the slacks and argyle sweater. I debated whether I should wear the heels, but going without would have meant tripping on the cuffs of the slacks and frigid feet. One last check in the bathroom mirror told me I might be passable as a boy. I put my disrobed things into the closet in my office, and then sat down at my desk and opened the schoolbook I brought with me to look as if I was studying.


My office door was part way open and she knocked, poking her head in. She didn‘t expect to see me. "Why, hello Dale" she said with surprise, opening the door the rest of the way. "I didn‘t expect to find you. What a pleasant surprise." She was dressed as she had been for school, in black slacks and an ivory cowl-neck sweater.

"Oh, hi there, Ms. Hunter… Yea… I actually work here one day a week" I replied.

"So — you‘re the assistant librarian that Melanie said could help me?" she asked, seemingly mystified.

"Yep… that‘s me" I replied, trying to sound calm and collected.

"Sorry. I guess I was expecting a girl" she said. I blushed.


She was there to find a particular book by one of the town‘s long-gone historians and poets. She asked me to help her find it.

"Sure, right this way."

Nervously, I rose from my desk, praying she wouldn‘t notice my dressing or heels. Shuffling my feet, trying to keep my heels from clicking, I led her to the section with the book she wanted. She was walking behind me.

"So, how long have you been working here?" she asked nonchalantly.

"Oh, two or three months" I replied.

"Good for you. I think it‘s wonderful that you work as a librarian."

I found the book she wanted. She browsed through it for a moment then asked me if there was somewhere where she could sit and look at the books. I showed her the two big overstuffed chairs by the window.

She sat down and studied the books for a few minutes as I went back to my office. Then she reappeared at my door and said pleasantly "I found what I wanted. Why don‘t you come and sit with me for a few minutes?"

I sat in the chair next to her and kept my feet beneath it, trying to hide my black velvet pumps.


We talked for almost an hour. We started chatting about class work, and the topic ended when she said "That‘s a beautiful sweater you‘re wearing — I‘m jealous. And your slacks, too — they‘re so, um, dressy… and the fabric looks beautiful."

I blushed and mumbled something about mother insisting that I dress nicely for work.

"Well, you‘ve certainly got some nice things."

She changed the topic and talked about music, then rambled around a bunch of other topics. What a combination she was! — Beauty and brains. I never could connect with my classmates on an intellectual level, but I could with Ms. Hunter. She was smart and witty and we were developing a repartee. We started talking about family. She asked me a bit about my mother, asking if she ever did any modeling, for she was so pretty. Then she told me about her family. She was ’now‘ an only child — she used to have a younger brother, but he died of a drug overdose. I expressed my sympathy. She told me how much she missed him and that I reminded her of him in many ways. "He was such a sweet and gentle boy, just like you" she said, adding "It was awful losing him and it destroyed our family. And all because of…" she trailed off; obviously, the memory was painful. Then she caught herself and finished with "Sorry… maybe some other time I‘ll feel comfortable talking about it."

We chatted a few more minutes. It was getting dark outside and getting near closing time. She stood to leave, saying she needed to get back home to grade some papers. She said she enjoyed talking with me, how nice it was to talk to such an intelligent and good listener — it had been years since she had such a good conversation with someone so sensitive and understanding. The last time, she said with a quivering voice, was when her brother was still alive.

She gave me an innocent kiss — a peck, really — on my cheek just before turning to leave.

"You smell really nice" she said, then turned and left.

I was staggered and numb. We had talked for an hour and the whole time I felt tingly. I had a crush on her, just like every other boy at school. If she only knew… or did she know? …that the whole time I was sitting there beside her I was completely crossdressed, wearing lacy intimates, ladies slacks and sweater, high-heel pumps. I didn‘t have long to ruminate on it, for Melanie buzzed me on the intercom after Ms. Hunter left.

"Did everything go alright, dear?" she asked.

"Uh, yea… We found her book and talked for a while."

"She seemed happy when she left, humming to herself. She‘s such a beautiful lady, don‘t you think?"

"Yes. Yes she is."

Melanie was closing up in a few minutes, so I could come downstairs whenever I wanted.

I changed back into the brassiere and padding, the skirt and sweaters, touched up my makeup and went back downstairs.


Melanie gave me a ride home. On the way home, I thanked her profusely for everything. "Don‘t thank me, Evelyn. It is me that should be thanking you — I had a wonderful time with you today dear."

When she pulled up to the house, Mimi came outside and insisted that she come in, offering her dinner.

"Sure — I‘d love to" said Melanie with a bit of hesitation. "You know I love your cooking, Mimi. But I can‘t tonight — I have a meeting I‘ve got to go to and I need to go home and get ready. Can I take a rain check?"

"Of course — how about Friday? We‘d love to have you over. You don‘t need to bring anything" replied Mimi.

"Friday it is. I‘ll come over after work."

"Wonderful!" exclaimed Mimi.


We had an early dinner and talked about the day and what a wonderful, accepting, and loving person Melanie was. I asked Mimi about her comment about me living as a girl once we moved to the Hamptons. She said she had said it mainly for Melanie‘s benefit but that it was something that we should discuss some other time. In the meantime, I shouldn‘t dwell on it. The big discussion was what I should wear to work next week. Mimi really wanted me to wear the poet‘s blouse, but wasn‘t sure what skirt I should wear — the black taffeta skirt was far too formal for a daytime dressing — perhaps mother had a skirt? I thought she might, I offered — a nice intermission length pleated black silk and wool skirt.

"We‘ll see, dear. Let‘s set aside some time between now and then to decide on your dressing" she said.

I told Mimi about Ms. Hunter, revealing as little as possible about her visit, other than I was relieved I was able to change into the sweater and slacks, and Ms. Hunter didn‘t say anything about the way I was dressed.

We made plans for the next day — Mimi wanted to drop me off at school early for she wanted to do some shopping in the city, saying "There‘s some particular things I need to pick up, but I thought I‘d splurge a little and buy myself some new clothes while I‘m at it." She might be back late and I should try to get a ride home if possible.

I was emotionally spent. I went to bed early, drained from everything that happened that day; the erotic morning with Mimi, having my couche-culottes felt as I was passing water, the tantalizing dressing for work followed by Melanie‘s acceptance and approval, knowing that I‘d be dressing as a lady librarian for Halloween and possibly after, Mimi‘s comment about me living full-time as a girl when we moved to the Hamptons. And, most of all, the whole encounter with Ms. Hunter and how well it went.

I went upstairs and did my nighttime routine of applying lotions and such. I wore my blue silk surah negligee and short robe. Mimi brought my bedtime tea just as I was sitting down at the vanity to brush my hair.

She was still dressed in her white blouse and long black rayon skirt.

I sat facing the vanity mirror, and Mimi sat on the tuffet behind me. She began to brush my hair. She was silent at first, sensing my mood. Then she began talking, barely above a whisper, slipping into a heavy French accent. She told me I was pretty, that my hair was beautiful, that I was her dear sweet princess, and that she loved being my nanny. Mesmerized with my reflection in the mirror and the simple pleasure of having my hair gently brushed, I became rather aroused beneath my couche-culottes.

"I really enjoyed being with you this morning, mon chéri. I like it that you and I share the secret of your bedwetting and that we can discuss it together. It brings us much closer, no? And that‘s important. It‘s our little secret, isn‘t it? And don‘t worry, dear, I won‘t tell anyone else. I don‘t want to tell anyone else — I want it to be our secret and no one else‘s."

She finished brushing my hair then pulled it back and tied it with the white silk ribbon, looping it around my cascading ponytail so it wouldn‘t get mussed in bed. She rose and turned down my bed and fluffed the pillows, then stood beside it, beckoning me to come to bed. I removed my robe, sat on the bed, and as I began to swing my legs up, she supported them so that my negligee wouldn‘t fold and bunch beneath my legs. I snuggled in and she drew the covers over me and tucked me in, leaning over to kiss me on the cheek.

"Pleasant dreams, my princess" she whispered. She turned out the lights and closed the door behind her.

It didn‘t take long before I creamed. Considering how long it had been since my last creaming, I was a little disappointed — it wasn‘t the toe-tingler I was expecting; I guess it was because I was so tired. So tired, in fact, that I didn‘t bother going to the bathroom to pass water -- I spent the night in wet couche-culottes.


Wednesday

There wasn‘t any time for our morning melodrama as we were leaving early. I woke early, took care of my couche-culottes, showered, and then dressed in my white silk charmeuse foundations and daywear, adding a couple of lacy panties for fun. Mimi helped me choose my outerwear, saying it was cold outside. I wore my black corduroy slacks, a heather gray cable-knit cashmere mock turtleneck sweater of my mothers, an earth-toned soft flannel shirt, my pair of black leather lace-up boots, and my navy blue wool pea coat. After a quick breakfast, Mimi dropped me off at a coffee shop near school as I had an hour or more before my first class.

I met up with Ms. Hunter as I walked to her class. She greeted me warmly and told me that she really enjoyed her time with me the day before. She was dressed in a beautiful brown sweater dress beneath her long black coat and I knew that most of the boys in the room were fantasizing about her during class.

Orchestra practice had been cancelled the week before, but since I was absent, I didn‘t know. So I had lunch off campus, then went to the school library and caught up on all my homework and turned in my assignments. I was able to get a ride home mid-afternoon and I called Mimi on her cell phone to let her know. She was still in the city and wouldn‘t be back until after dinner.

"You should take a nice nap, dear" she said just before hanging up.

I took her advice and went upstairs to my boudoir and had a delightful creaming, letting my cries and moans reverberate in the empty house.

Afterwards, I dressed in the velvet burn-out dress and came downstairs with some laundry. The new camera we had ordered had arrived and I spent an hour or so trying it out so that I could show Mimi how it worked. I made dinner, did a little ironing, and was about ready to start my nighttime routine when Mimi arrived. She was a bit frazzled from the day. I doted on her, fixing her some tea as she relaxed on the couch and watched some television. I asked her about her about her day. I didn‘t know what her errands were in the city, nor did I ask directly, but she offered that she had gone to a couple of specialty shops and done a little shopping for herself, among other things. She seemed pleased with her day.

I showed her the new camera and she tried it out.

"Oh, this is fabulous, Evelyn. You made a good choice" she said after a few minutes of using it. "Perhaps you‘ll let me photograph you wearing some of your intimates, no?" she asked with a wink. I let the suggestion slide, but was secretly looking forward to it.

I told her about getting all my homework done and my assignments turned in, and then suggested that I could just stay home the next day. She readily agreed. "I‘ll be working tomorrow, but I don‘t have to leave until late morning. I‘ll be able to bring you your morning tea" she offered. I couldn‘t help but think that she was hinting that we could play our little morning melodrama.

The evening ended in my boudoir with me in my white crepe-de-chine chemise, dance pantie, and long robe and Mimi in her tartan robe and creamy white ballet dress. As she had done the night before, she brushed my hair, sitting on the tuffet behind me, then turned down my bed, fluffed my pillows, guided me into bed, and tucked me in.


Thursday

I woke when I heard Mimi coming up the stairs. She soon appeared, carrying a tray with a pot of tea, scones, fruit, and yogurt. She was still wearing her tartan robe. As I sat up in bed, she poured a cup of tea and handed it to me, saying "I‘ll be back in ten minutes or so, dear, and we can discuss your day. But I‘ve got something new I want to change into first."

As soon as she left, I got up and brushed out my hair and put on a bit of makeup and a dab of perfume, sipping the tea and recognizing the taste of Mimi‘s special blend. It didn‘t take long before I was pausing to wet myself — after all, my couche-culottes needed to be at least a little wet when Mimi came back. I got back in bed, my robe tied loosely, and sat up with my legs tucked to my side, the covers drawn up to my waist, sipping my second cup of tea.

Mimi arrived shortly. She was wearing a beautiful new robe made of a powder blue rayon foulard. The robe was a long kimono style with royal blue satin trim on the sleeve cuffs and neckline, embroidered vines in contrasting blue colors, and tied with a royal blue satin sash. She had primped a bit as well, brushing her hair and putting on some lipstick.

"That‘s gorgeous, nanny" I said softly.

"Why thank you, dear. I bought it yesterday along with some other things" she said, smiling. "I‘m glad you like it. Let me show you the nightgown" she said nonchalantly, untying the sash and opening the robe. The empire waist nightgown had the same powder blue rayon foulard fabric. The bodice was light blue pleated georgette over white lace netting with a bit of a surplice wrap. The waist was decorated with a royal blue satin ribbon tied in a bow with long streamers and the long skirt had the same embroidered vine design as the robe. The bodice fabric barely concealed her breasts and I must have stared slack-jawed for a moment before she asked if I liked it.

"Oh, it‘s beautiful nanny" I said, trying to think of something more to say, finally coming up with "…I‘m jealous…"

"You‘re so sweet" she said, sitting down on the bed so that she faced me. She fluffed up a pillow and put it behind me, adding to the pile I was leaning against. She filled my tea cup and handed it to me. I drank most of the cup as she brushed back a bit of my hair and gave me a concerned look as she asked "How are you dear? Did you have problems last night?"

I set the cup down on the nightstand the whispered "Yes… yes I did nanny," looking down. "I… I wet myself again."

"Oh, you poor thing" she said, her voice playfully dripping with sympathy.

And so our morning melodrama began.

I hadn‘t planned on the turn of events that happened next. The familiar pre-release chill came over me quite quickly and rather than just hiding the act of passing water, I decided, on the spur of the moment, to spice things up.

"Nanny?" I whined, biting my thumbnail "I… I have to go…"

"What do you mean, dear?" she asked, again with a playful but concerned tone.

"I… I have to go… you know… go and pass water… the tea, you know…" I said, my voice faltering. I shifted my position, preparing to leave the bed and go to the toilet.

She let my words hang in the air for a moment or two. I detected a wry smile as she gently stroked my shoulder and in a soft voice said "But we were just getting comfortable, mon chéri. Wouldn‘t you rather stay here with me?"

"Uh huh" I whispered.

"Are you very wet?" she asked.

"Umm… not really, nanny" I replied, wondering if she was going to invite me to wet myself as she sat with me.

"Well then… if your couche-culottes can take more wetness, couldn‘t you just wet in them and stay here with me instead?"

"Oh" I whispered, twisting a bit of my hair around my finger, my eyes wide. "I guess so… I could do that, nanny… I mean, if you don‘t mind…"

"Of course I don‘t mind, dear" she replied sweetly. "Are you close, dear? Close to wetting yourself?" she asked, gently rubbing my shoulder and then fingering the lace lapel of by robe. Her eyes were searching mine.

"Yes, nanny… very close…" I replied in a quavering moan.

"Go ahead dear… let it go…" she whispered, adding "…it‘s alright dear… I understand…"

The moment arrived. I drew my breath and quivered, my eyes rolling back for a second. The release came and I exhaled "Oh… oh nanny."

"That‘s right… let it go…"

"Oh" I moaned, inhaling, and then letting out a satisfying sigh. She watched me intently for a moment.

"Perhaps we should look" she whispered as she began slowly rolling back the bed cover to expose my dance panties. "After all, you don‘t want to wet your things, do you?" When she finished rolling back the covers, she whispered "open your robe, dear… let me see."

I pulled the streamers of the knot around my sash and opened my robe, sitting up a bit as I did. Mimi was looking down at my waist, contentedly humming to herself. The chemise covered most of the dance panties.

"Raise your chemise so I can see, dear" she said, clasping the hem of the chemise and lifting it up off the dance panties. I instinctively took the hem and pulled it up to the waistline of the panties.

"Oh nanny — it‘s just starting, nanny" I moaned, both of us looking down at my panties.

"Are you having trouble letting go, dear?"

"Uh huh… maybe a little, nanny."

"Try and relax. Maybe if you sat up a bit…"

I straightened up so that my legs were beneath me, facing Mimi, holding up my chemise to fully show my panties, looking down. My robe fell from my shoulders.

"Maybe this will help" she said, running her finger down nape of my neck, causing me to quiver. I gave a little gasp, but said nothing. Everything was still and quiet in the house, just my nanny and me in my bed, both dressed in our bed things, both of us fixated on having me pass water into my couche-culottes.

Mimi stroked my neck for a long moment, and then asked "You‘re having difficulties, aren‘t you dear?"

"Uh-huh."

"Here…" she said, shifting our positions so that she was now behind me. She put one arm around my shoulder and the other on the side of my head, and then guided me to her breasts. She stroked my hair.

"There, there, dear… It‘s all right… let it go…"

I noticed that her nipples had become pronounced. I put my hand on her shoulder. My index finger glided along the strap of her nightgown for a moment or two. She patted my head and stroked my hair and I was able to finally empty myself.

"Umm…" I purred, "I‘m doing better now, nanny." I had passed most of my water and was now at the point where I couldn‘t tell if I was still wetting myself.

"How are your couche-culottes, dear? Are they very wet?" she asked in a soothing voice.

"Uh-huh" I purred.

"Maybe we should check you now."

"Alright" I replied. She unfolded her embrace and guided me back to a sitting position. She had me lift my chemise again to expose my dance panties.

"Oh nanny… I hope my panties aren‘t wet" I lisped.

She fingered the stocking suspenders and the hems of my panties.

"So far so good, princess" she said, looking up. "Take your panties down for me."

I slowly drew down my panties to expose the plastic panties. She repositioned herself and had me lean over, my elbows on the bed, my derriá¨re elevated. She gathered my robe and let it fold and fall off the small of my back. I turned my head towards the mirror and had a full view of myself and Mimi through the strands of my falling hair. Her hand glided down to my derriá¨re cheek. She wasn‘t looking in the mirror and I watched her expression as she glanced over me, a smile on her face. With her other hand, she gently stroked the skin between her cleavage and then brushed her fingers across the hard nipple of her breast, letting out an almost imperceptible sigh.

"Oh nanny" I whispered "You were so right about me being a bed-wetter… I really do need to wear couche-culottes, don‘t I?"

"Yes, yes you do" she replied sympathetically. "But I knew that you would, dear."

As she had done the previous morning, she pinched together some of the plastic panties and the terrycloth and announced that I seemed quite wet. I was delighted when her hand slid down — she was going between my legs to investigate the pad.

"Oh nanny…" I lisped as her hand came to rest over the pad. She let it linger there.

"I‘m going to give your pad a squeeze, mon chéri… are you ready?"

"Yes, nanny…" I breathed.

She pinched the pad, releasing its warm contents. I moaned. She released it then pressed with two fingers firmly in the middle of the pad and walked them upwards along the length of the pad. When she reached the end of the pad, she continued walking her fingers up and over until she reached my waist. I gasped and moaned.

"Well, you are wet, aren‘t you?" she asked coyly, patting my derriere.

"Yes, nanny…"

"But I think you‘re safe for a little while longer; but if you have to go again, be sure to tell me, alright? In the meantime, let‘s take off your panties, just in case."

She slid my panties down to my knees, then had me lift one leg slightly, sliding the pantie down past my knee, and then repeated the procedure with my other leg. With the panties past my knees, she slid them past my ankles and off my legs. She smoothed them out on her lap and set them aside as I rose from my position. She helped me bring my robe back up to my shoulders. I sensed that the intimate part of our melodrama was coming to an end.

"When I was in the city yesterday, I visited a little specialty shop where I ordered some new couche-culottes for you. They are much more suitable for you than these. They should arrive in a few days, along with some other things. Until then, we‘ll just have to be careful that you don‘t wet yourself too much, alright?"

"Uh-huh" I replied, wondering what she meant by ’more suitable‘.

"Now… Evelyn? I‘m concerned about you being home all by yourself today. I really wish I could stay here with you all day and make sure you‘re staying on track and dressing as a suitable young lady. But I can‘t. So I‘ve been thinking: your mother bought you another pretty outfit before she left, but we decided not to give it to you right away, but to wait for a special occasion. I‘m thinking you could wear it for dinner with Melanie tomorrow evening."

"Really?" I replied, genuine excitement in my voice — a new dress!

"Yes, princess. And what I was thinking that if I give it to you today, I know you just won‘t be able to resist spending most of the day dressing up in it and choosing just the right accessories. I‘ll know that while I‘m away, you‘ll be dressing properly. I think it‘s a good idea, don‘t you?"

"Oh yes, nanny" I said, excited to have a new ensemble to try on. I asked her to describe the new outfit, but she wouldn‘t. Instead, she said she wanted to change the sheets on my bed and have me bathe.

We stripped the sheets off my bed then clothed it with the petal pink satin sheets and pillowcases. I took the sheets, along with a fresh pair of terrycloth panties, and went downstairs to clean up. Returning upstairs, I found that Mimi had started my bath. She said that while I was bathing, she‘d get ready for work then come and get me and, she said with a wink "…finish planning your day."

I ate the breakfast that Mimi had brought me earlier then slipped into the bathtub. I was so creamy and dreamy and full of delicious anticipation— my daintie was fully stimulated as I bathed — I had to control myself. After finishing my bath, I applied my lotions and powders, donned a fresh pair of terrycloth panties, wrapped myself in my warm terrycloth wrap, bathrobe, and turban, and sat down at my vanity to apply my foundation makeup.


Mimi soon arrived. She was wearing another new robe, dusty pink with black trim, made of a soft fabric that looked like a cashmere blend. She explained that it was something else she had purchased in the city the day before.

"Would you mind helping me finish dressing, dear?" she asked as she stood behind me at the vanity. I followed her into my mother‘s room. On mother‘s bed lay a purple sweater, Mimi‘s gray pleated skirt, and a full slip. The soft sweater had a surplice bodice, full length raglan sleeves, and knit with a flattering ribbing. The full slip was a hot pink jacquard satin with black lace accents.

I sat at my mother‘s vanity and watched as she removed her robe, revealing a new set of foundations — pink with ornate black lace; a demi-cup brassiere, a long waist-cincher, and briefs, matched with a pair of black stockings. "It‘s a new set… do you like it dear?" she asked, taking a seductive turn.

"Oh, nanny…" I lisped. She just smiled.

I noticed that her waist cincher was not clasped properly in the back so I offered to fix it for her. It required that I unclasp the top half and start over, struggling with the hook and eye clasps.

"Here — be a dear and help me with this" she said, handing me the slip. I stood in front of her, rolled the slip, and guided it onto her outstretched arms and onto her shoulders, positioning the straps as I did, then took the hem and drew it down her body.

She had me open her skirt and kneel on the floor as she stepped into it. She drew it up while I held the hem of her slip. Then I moved behind her and brought the skirt to her waist and zipped it. She drew the sweater over her head and I helped guide it down and adjust it.

"You look fabulous, nanny" I said honestly. "That sweater is so pretty on you."

"Thank you dear. I‘m glad you think so. It‘s important to me. Your mommy wouldn‘t mind if I borrowed one of her necklaces and maybe a scarf, would she?"

"Of course not" I replied. She sat down at the vanity while I picked out a few things for her to try, settling on a necklace made with variegated purple silk ribbon with a long triangular pendent made of gold and pink colored glass. We tried a couple of scarves but decided they detracted from the sweater. Then I helped her into her black suede pumps, kneeling on the floor in front of her.

"It‘s so nice to have a fine young lady attend to me" she said. She stood and took a few turns and asked "How do I look, dear? Do you approve of how your nanny looks?"

"Oh, yes nanny!" I blurted out.

"Wonderful! You know, I think you should start suggesting what I should wear more often. You have such good tastes. And when we‘re here by ourselves, I think you have the right to suggest something you want me to wear. Is it a deal?"

"Okay… Sure… I‘d love to, nanny" I replied a bit cautiously, adding "I think you always dress wonderfully."

"That‘s good. But I‘m always open to suggestions. Just tell me what you like. I like wearing my sets for you" she said as she moved toward the door. "Now, dear, you wait right here while I fetch your new ensemble and bring it to your room. Then I‘ll come get you."

She kissed me on the cheek and left me. She had left her robe on the bed and I inspected it — it was a wonderful blend of cashmere, wool, and nylon, so delectably soft. I was glad for Mimi — glad that she enjoyed nice things as I did. I sat at the vanity and unwrapped the turban from around my hair. I slowly combed my hair, waiting on pins and needles for my nanny to come and get me.

The knock came and she took me by the hand down the hallway to my boudoir. "I just know you‘re going to love this, Evelyn. And I won‘t have to worry about you while I‘m away today, either; I know you‘ll be dressing up all nice and pretty and not upsetting yourself about other things."


Hanging on a padded hanger on the dressing screen was a calf length black silk brocade wrap dress. The brocade pattern was of intertwined spirals that somehow suggested an oriental motif. The basis of the brocade was a lightweight velvety silk, and the jacquard pattern was shimmering blue-black. The dress was finished with one inch shimmering blue-black satin trim at the wrap of the bodice and the cuffs of the three-quarter length notched sleeves. The wrap closed with a big blue-black satin bow with two long streamers descending to the hem. A rhinestone buckle was fitted to the middle of the bow. On the floor beneath the dress was a pair of three inch black satin-finish Sabrina heel pumps, open toe, with white banding at all the seams. Next to the pumps was a matching rectangular clutch purse.

I squealed with delight as I took it down and held it up. "Oh nanny! It‘s beautiful!" I squealed. The dress was lighter weight than it looked — the hand of the fabric was like a whisper against my skin. Mimi stood behind me, smiling, saying "See? I knew you‘d love it." I hung it back on the dressing screen and gave Mimi a hug. She held me close, pulling my head to her breasts.


"That‘s not all dear" she said, releasing me. "Look on the bed".

There were two silver paper boxes on the bed, wrapped with silver tulle ribbon. There was also a small bag with pink tissue puffed out the top.

"Come, let‘s sit while you open them" she said, making her way to the bed and sitting down. I sat next to her and she handed me the first box. I untied the ribbon and let out a little cry as I lifted a black negligee made of a shimmering black jacquard material with profuse antique white Rosaline lace trim at the bodice and hems. It had a plunging back with delicate crisscrossed straps. Beneath it was a matching cocoon jacket.

"Yes, it‘s a negligee — but it can double as a slip for your dress" she explained.

Stretching out on the bed, she handed me the next box. Inside was a backless and strapless brassiere, the front covering to the midriff with a hook and eye closure in the back, made of black satin with profuse white embroidery. I lifted the brassiere out of the box, and discovered a matching waspie beneath. I could see that the waspie and brassiere would slightly overlap each other to make it appear as almost one garment. Beneath the waspie were matching briefs and a tanga pantie. These treasures were followed with two pairs of black seamed stockings with Cuban heels and lace tops, one pair with an embroidered ivy design in black running up the side from toe to thigh.

The look in my eyes must have said everything. Beneath my terrycloth panties, my daintie was fully stimulated — I had to make sure that my robe hid what I was feeling.

Mimi handed me the colorful gift bag and I removed the pink tissue. First was a couple of music CDs, one titled "Private Dancing" and another titled "Rainy Day Romancing."

"Those are from me, mon chéri. I came across them yesterday and immediately thought of you" she said quietly.

"Oh nanny…" I whispered. I scanned over the descriptions and titles. Both promised romantic and seductive music for intimate moments and one proclaimed it was "music for lovemaking".

A velveteen jewelry box was next, containing a black onyx stone set — necklace, earrings, bracelet; each triangular onyx piece set off with sparkling rhinestones. Then a pair of black hair sticks with a big crystal bead on the ends followed by tufts of black marabou, a big red silk rose hair clip meant to wear on the side, and another hair clip, this one black organza ivy with lots of stems with sparking crystals at their ends.

"What do you think, dear?" asked Mimi coyly.

"Oh… oh nanny, I don‘t know what to say… thank you… thank you so much!" I blurted.

"That‘s alright precious — your eyes say everything."

She sat up and turned me towards her, gently stroked my arm and said "I want you to have fun today, princess — dressing up in your new things. Now… I don‘t want to see you wearing this when I get home this evening — save it for our dinner with Melanie tomorrow, okay?"

"Yes nanny. I‘ll wear something else for dinner tonight" I replied gratefully, for I didn‘t want to over-wear the ensemble.

"Now, before I go, would you let me help you into your new bra and waspie?"

I hesitated for a moment. The brassiere wasn‘t an issue — not anymore given the dressings she had gave me, but in order to put on the waspie, she might see what was going on beneath the terrycloth panties. She sensed my hesitation and said in a whisper "You are wearing panties, aren‘t you dear?"

"Uh huh" I breathed.

"Well then… I have an idea — you can lay on your tummy while I fasten up your waspie" she whispered with a smile. My immediate concern was that I‘d cream if I rolled onto my tummy. Maybe I‘d be able to calm my daintie, I thought.

She tugged at the sash that held my robe together, but it didn‘t loosen, so I took over, untying the sash and letting the robe fall from my shoulders. She slowly wrapped the brassiere around me and fastened it in the back. The waspie came next; my robe was all bunched around my waist so that she couldn‘t see my panties. She wrapped the waspie around me and clasped it at the top.

"Now lie on your tummy for me dear" she said very gently.

I managed to lie down without her seeing my stimulated state. She knelt to my side and I watched in the mirror as she swept my long hair aside and repositioned the waspie a little and began to fasten the hook and eye clasps. I concentrated on not letting the moment culminate with me creaming into my panties.

"Now, my dear, I want you to have a nice time today. I don‘t want you to dwell on any upsetting or unpleasant thoughts. You know what I mean — thoughts about your bedwetting problems or of being an inadequate boy, or being ashamed to be all dressed up in such pretty things. I want you to just enjoy being a well-kept young miss. And be sure you take a nice nap, too… in your big bed with its fine sheets and pillows. And don‘t forget to wear your couche-culottes when in bed — we don‘t want any bedwetting accidents now do we?"

"No nanny" I whispered.

She patted me on the derriere and said "That‘s a good little girl." She draped the chenille throw across me, then she rose and drew the curtains on the windows and moments later left the room.


I lay motionless on the bed, almost panting. I sensed Mimi‘s car drive off and I still didn‘t move. I looked at my refection in the mirror and my thoughts tumbled from one thing to another. I was completely under Mimi‘s spell — why was she doing these things to me? — or for me? There had to be another agenda to her actions other than to ’make me feel comfortable as a lady‘, something far more than mother could have planned on. Her sexual innuendos and actions were certainly an unexpected but welcome surprise, like how her nipples became hard, how she took me to her breasts, how she ’checked‘ my couche-culottes, the things she was dressing in, showing me her nightgowns and underthings, and encouraging me to take a nap, knowing full well what I would be doing with myself in bed with my pillows. I didn‘t know where it was all going, but every bit of me wanted to go there. Why was I letting her do these things to me? The answer to the last question was simple — because I was weak and submissive and every part of me adored being a well-kept young lady. There was no way I could resist, and that was the shameful part. I began to cry a little, disgusted with myself and what I was letting her do to me. Was it true what Mimi said? That my mother wanted me to live full-time as a girl when we moved to the Hamptons? What about my step-father? Would Mimi move with us and be my nanny?


I forced myself to stop thinking about these things and think about mundane boring things instead. I eventually drifted off to sleep for a few minutes, and my daintie finally relaxed.


After filling out my brassiere with my sachets, I drew my blue cashmere robe around me and immediately thought of Auntie. She, too, wanted me in fine dresses and lingerie. But she was a continent away and, compared to Mimi, had little influence on me.

I inserted the CDs in my stereo; the music was kind of new age with slow seductive beats and breathy female vocals that sometimes drifted into moans and sighs. It was unabashedly erotic, and I was stunned that Mimi had so nonchalantly given it to me.

I proceeded to dress in three phases. First I did the things that required attention to fine detail; making up and applying polish to my nails. I sat at my vanity and brought out my eyelashes as long and luxurious as I could, applied eyeliner and eyeshadow in hues ranging from dusty rose to charcoal to deep dark blue, and brushed on face powder that contained just a hint of sparkle. I sculpted my lips using a blush pink lip pencil and applied a layer of light pink moisturizing gloss. I would wait until later to finish with cheek blush and a deeper lip gloss. Then I polished my finger and toe nails deep red.

My next phase was to finish my underdressing and sit at the vanity doing my hair, the last of my makeup, and don my jewelry. But first, I partook of my hashish, taking several deep tokes. Oh my, but I was quite elevated when I began dressing. Off came the terrycloth panties, moist from my creamy daintie. On went the cashmere glove and the new tanga panties. With ’oohs‘ and ’ahhs‘, I slowly drew on the black stockings with the vine pattern and then matching briefs.

I was titching and moaning with the music as I slipped into the beautiful negligee, carefully negotiating the maze of delicate crisscrossing straps, almost swooning as the luscious fabric spilled over me. After admiring myself for a minute — the black fabric and white lace really accentuated my pale alabaster skin — I donned the cocoon jacket. Then I sat at the vanity I put my hair up in a loose bun, positioning and fixing the bun with the hair sticks. I used some mousse and curling iron to create profuse ringlet curls in the many strands of hair that were not caught by the bun. My thoughts had returned to Mimi and the upsetting thoughts she told me not to think about — my bedwetting, my inadequacies. Yes, I was such an inadequate boy — so much better suited to being a well-kept young lady.

The rhinestone and onyx jewelry came next and my mood began to change — I was reveling in the moment again, saying my O‘s. The music was really setting me off. I was so charged, so ready for the next phase. I brushed on soft pink cheek blush powder. I finished my lips in deep glistening red. What a memorable dressing it was that was unfolding.

To begin my final phase, I partook of just a little more hashish and a small glass of sherry. In the soft curtained light of my boudoir, I sat and put on the open-toed pumps. Such high heels! They fit perfectly — I was so lucky that my mother‘s shoe size and mine were the same.


It was time for the dress. I slipped into it without the benefit of a mirror, fastened the wrap and then the satin bow with the rhinestone buckle, my eye catching the long streamers as they fell to the hem of the dress. I smoothed out the dress and looked up, still avoiding the mirror. I took in my boudoir — the beautiful bed with my initials monogrammed on the bedcover and pillowcases, the satin sheets, the fine antique furnishings, the impossibly feminine porcelain figurines, and the framed photographs of a beautiful and fetching young lady in her finery. It was hard to believe it was me in the photographs.


The moment arrived. Taking the purse in one hand, I sashayed in rhythm to the music and presented myself to the mirrors.

"Oh Evelyn" I whispered, "Oh my, just look at you. Oh my…" The ensemble was just so elegant, so dramatic and vivid, so very… everything. The rhinestones sparkled, even in the soft glow of the dim light. I was dressed for a dinner date at a fancy restaurant. I don‘t know how long I stood there, just titching and saying my O‘s, my daintie throbbing in her cashmere glove. I had intended to try some different accessories, and I knew that I‘d have to tone down the ensemble for dinner with Melanie. I had a couple of ideas. But accessorizing would have to wait until later, for ever so slowly, my movements brought me closer and closer to creaming. The house was empty, the neighbors far away, all else was still and quiet except for the exquisitely dressed lady dancing in the mirrors. My cries became louder and louder until a shuddering climax rent my entire being, sending me into a realm of ecstasy I only dreamed of existing.


It took some time to gather my wits. I had sullied my panties but, fortunately nothing else. My creaming had been so deeply satisfying and the memory of it made me smile broadly. I hummed happily as I undressed and slipped on couch-culottes and my terrycloth robe and went to the sink to wash my sullied panties and daintie glove. Putting my hands in the warm water caused me to wet myself. Eventually, I donned the lilac chiffon peignoir and snuggled into bed. After a short nap, I woke and had fine time creaming again, this time into my damp couche-culottes.


I bathed and spent the next couple of hours dressing for the evening. It took me a while to decide on what to wear. I was feeling so devil-may-care, and I convinced myself it would be alright to wear the georgette crepe sailor‘s dress — white blouse and white skirt — revealing my light navy blue silk surah with white Venise lace chemise and tap pantie, my garter suspenders clasped to the top of my white silk stockings. I felt so naughty and wondered what Mimi would say. I told myself I would replace the chemise with the matching negligee before Mimi came home. I had a fine time choosing accessories, and ended up in pearls, a white lace scarf tying my loose ponytail, and a pair of mother‘s blue and white patent leather pumps. I had redone my fingernail polish to more of a bluish plum color and my makeup with silvers, blues, and plums.

It was almost time for Mimi to come back when I had finished dressing and primping. She had been right about not having to leave my boudoir — I had spent the entire day there, except for a foray to mother‘s room for the shoes and scarf. I went downstairs to greet her when she came, daring myself not to change into the negligee — it would have been such a bother. I was sitting on the couch, a fire going in the fireplace, thumbing through a fashion magazine, when she arrived. I rose to greet her and help her out of her coat.

"So tell me, dear, how was your day?" she asked.

"Wonderful, nanny; I had a really nice time. I just love the new dress and things."

"Did you have a nice nap?"

"Uh-huh" I replied with a bit of a smile, the memory of my two creamings still fresh in my mind.

"Good for you dear."

She looked me over and said "That‘s such a cute dress, Evelyn. Not exactly a winter dress, is it?"

"No, it‘s not. But I wanted to wear something new for dinner. Besides, it‘s warm enough inside."

"I like it. You‘re really cute in it. It‘s something a young girl would wear… a pretty dress her mommy bought for her for a cruise. Except… I can see your lacy little intimates" she added with a smile. "Maybe your mommy and you will go on a cruise someday… it would be perfect set to wear for a stroll on the promenade deck."

The thought of going on a cruise and strolling on the promenade deck in the dressing sent chills through me. I blushed and stammered something about how I should be wearing a slip or petticoat with it.

"Sure… you could do that… but there‘s nothing wrong with showing off a bit."


The day ended with me in my white silk charmeuse pajama and robe set and Mimi in her tartan robe and black ballet dress watching a television program Mimi liked, both of us curled up on opposite ends of the couch. We made plans for the next day; Mimi wanted to visit the dairy she liked to pick up some cheese and wanted me to come with her. Melanie would be coming over between five and six o‘clock. In between, Mimi said there would be plenty of time for me to take a nap and get ready for dinner.


Friday

I was up and about early to give myself plenty of time to dress for our excursion to the dairy. Mimi seemed to be expecting me to be up early — when we greeted each other downstairs for breakfast, she offered, in an apologetic tone, that there would be time tomorrow morning for her to "come and visit with you before you start your day."

I had decided on wearing mother‘s oatmeal colored ribbed angora and lambswool sweater dress with the mauve trim and waist sash. I bathed and powdered, polished my nails in a pink that closely matched the mauve trim of the sweater dress, and made up with hues of pinks and plums. I wore my hair long, sweeping a bit of it back with the tortoise shell hair clip. As I did the last time I wore the dress, I chose the side-zipper all-in-one girdle to lift my derriá¨re and flatten my tummy, and selected the lingerie pink set with the ivory Venetian point lace trim and embroidery; camisole, pettislip, and dance pantie, along with white opaque stockings. I accessorized with mother‘s artisan jewelry in ivory and mauve tones. Instead of pumps I chose mother‘s pair of calf-length boots in creamy beige kid leather and two-inch Cuban heels, along with a beige leather over-the-shoulder purse. It was chilly outside, so I added my mother‘s off-white wool trench coat and an oh-so-soft angora scarf, glove, and beret set in white.

I was sitting at my vanity doing my makeup, having dressed to the camisole and dance pantie with the short pink robe when Mimi knocked on the door. She was already dressed in her nice black wool suit and white crew neck sweater.

"How about a few pictures of you getting ready?" she asked gaily, holding up the new camera.

She took some shots of me at sitting at the vanity then had me stand by the bedpost, robe open, my arms behind me, my leg cocked at bit. I timidly struck a few other poses. Then I followed her downstairs to show her how to upload the photos to the computer, launch the photo editing software, and do basic adjustments. I was quite taken by the photos she took of me in my underthings. She told me to go finish dressing while she played with the software.

I finished dressing and came downstairs. Mimi showed me what she had learned about editing the photos — she had moved beyond the basics.


It was exciting to be going out again. It wasn‘t nearly as nerve-wracking as our previous excursions. I didn‘t even slouch down in the seat as we drove off. On the way to the dairy talked about digital photography. Mimi wanted to try her hand at ’boudoir‘ photography with me as the subject, telling me that I‘d treasure the photographs as I became older.


There were no other customers at the dairy when we pulled up. Mimi convinced me to come inside with her. I was feeling a bit of confidence — I knew the layout of the delicatessen; the seating area was nothing more than a few wooden tables — very clean and utilitarian. I could sit inconspicuously at a particular out-of-the-way table while Mimi perused and selected cheeses and such. Mimi reassured me by saying "I‘ll be there for you." So with my heart racing, I followed her into the delicatessen and immediately made my way to the table I had in mind. Mimi made things easier by announcing "I‘ll be a minute dear… why don‘t you sit here and wait?"

There was a woman and a college-aged boy behind the deli counter — I gathered that he was her son. I became aware that he was casting lots of glances my way and I found myself blushing and looking away. After Mimi had made her selections, she asked "Evelyn, dear? Why don‘t we get a couple of sandwiches and just eat here?"

I didn‘t want to answer — I thought my voice might give me away. Nor did I want to get into a long discussion with her about leaving. So I replied with a quiet "Okay". The young man seemed pleased. Thankfully, Mimi didn‘t make me go to the counter to place my order; she walked over to me and asked what I wanted. After placing our orders, she came and sat down with me, smiling. The young man brought us our drinks. I avoided looking up at him or speaking anything more than a simple thank you. I took off my white angora gloves, forgetting that my nails were polished pink. Mimi patted me on the hand and whispered that I was doing fine. The young man brought our sandwiches and made an attempt to start a conversation with us — me in particular — saying something about the weather. I mumbled something, too embarrassed to engage him. Just then, some older couples came in and he had to go back to the counter. The scene was no longer so intimate and I relaxed, melting into the background. Mimi whispered that she thought the young man was handsome and that he was obviously interested in me. "You have no idea how pretty you are…" she said.

We paid our bill and left unnoticed. Back in the car, I felt a wave of relief and exhilaration. One more small step going out in the world as a young lady. One more chink out of the wall that surrounded me.

"I was really nervous, Mimi, but I guess I did alright, huh?" I asked as we drove off.

"Oh, Evelyn, you did just fine. For goodness sake, all you need to do is to relax and be yourself. That young man certainly thought you were cute — he kept looking you over… didn‘t you notice?"

"Uh, yea" I replied, blushing.

"That‘s something you‘re going to have to get used too — admiring glances from both men and women. You‘re just so pretty and fetching."


One the way home, Mimi stopped off at a florist for some fresh flowers while I sat in the car and touched up my makeup. When we got back home, a wave of euphoria came over me — I had gone out again and rather easily passed as a young lady. Mimi took some pictures of me outside standing in front of our door. Back inside, I busied myself for a half hour or so, helping Mimi arrange the fresh flowers and bringing out our china for dinner. She disappeared upstairs for a bit, and when came back down, she said "Well, Evelyn, you‘ve had an exciting day so far, haven‘t you? I bet you‘re a bit tired. You should go upstairs and have a nice little nap. I turned down your bed for you. I‘ll come up in a couple of hours and wake you so you can get ready for dinner tonight. I‘ve got a few things I need to do then I think I may lay down a bit, too."

I didn‘t need any further encouragement, so I made my way upstairs carrying my coat and scarf set. Mimi had turned down the bed and laid out my lilac peignoir and robe set and a set of couche-culottes. It took me a few moments to realize she had done something else, too. The bed coverings and sheets were turned halfway down the bed and revealed part of my big monogrammed pillow placed in the center of the bed. I thought back to the previous Sunday and how she had discovered me lying on top of the very same pillow. With a little gasp of discovery, I realized she must have put it there for me to lie upon… to cream upon… Then I noticed my hand mirror on the nightstand.

"Oh, nanny…" I whispered, gliding my finger over the pillow.

I went to the bathroom and partook of just a bit of my stash, then donned the coat, scarf, gloves, and beret so I‘d be dressed just as I had been when I was out. I presented myself to the mirrors and whispered "Oh Evelyn — you went out like this?"

I began to slowly undress, first gently pulling off my white angora gloves, and then opening my coat. I had the naughtiest thought that I was undressing for the young man at the delicatessen. My feelings were all jumbled and confused about this — I didn‘t think of myself as homosexual because I was a lady, but obviously…

After undressing and freeing myself of the tight body-contouring girdle, I slipped into lilac chiffon and stood by the bed, struggling with the fact that my nanny had laid out a pillow for me… How could she? She knew! Of course she knew!

I slowly lifted the covers off the pillow, revealing a neatly folded white velour hand towel from our linen closet.

"Ewww…" I moaned.

I unfolded the hand towel and draped it over the pillow, then climbed into bed, positioning myself over the pillow, lifting my chiffon, and moaned again as snuggled onto the pillow.

A few minutes of delicious slow churning and quiet O‘s followed. Then I heard Mimi coming up the stairs and lay stock-still, wondering if she was coming my way. The door was locked, but if she came to check on me… I heard her walk the other way towards my mother‘s room. I sat breathlessly, not daring to continue my pleasures. I took the hand mirror and primped a bit, then used it to examine my reflections in the other mirrors. A minute or so passed and I decided that she must have either gone back downstairs, or she was using my mother‘s bed for her nap.

I couldn‘t contain myself any longer, so I began anew my delicious churning and soon completely forgot about my nanny and where she might be, letting my O‘s escape my lips as I tried to prolong the beautiful agony. I delayed my approach to the precipice as long as I could, but it came closer and closer and I let out little squeals and yips, and, as the moment arrived, gasping and moaning and finally a loud "Ohhhh…"


I was awake and dressed in my terrycloth bathrobe, just getting ready to bathe, when Mimi arrived at my door with coffee and scones. She was wearing her blue checked robe and black ballet dress beneath.

"Did you have a nice nap, mon chéri?" she asked, setting the tray on the table between the wingback chairs.

"Yes, nanny" I replied softly, thinking about the pillow, towel, and hand mirror, hoping she wouldn‘t mention it.

"Good. It‘s important you have a nice nap" was all she said before turning the conversation to my evening ensemble. I confided in her that I thought the new black velvet dress was too formal for a simple dinner with Melanie. She assuaged my concerns by saying she was confident I‘d pull it off and, in the end, radiate simple understated elegance. I asked her what she‘d be wearing and she said she hadn‘t decided yet. Melanie, she said, would be coming directly from work and would probably look nice as she always did.

In the end, I was satisfied with my dinner ensemble. By removing the glitzy rhinestone buckle from the waist sash and tying the sash in a simple bow, the mood of the dress changed from dramatic eveningwear to a tasteful dinner dress. I wore my hair down, gently swept back and fastened with a simple black satin barrette of my mother‘s. I went light on my makeup, opting for a soft look, left my fingernails in their pink polish, and wore my pearl necklace and earrings and a couple of ivory bracelets. My stockings were black silk and without seams. However, I couldn‘t resist wearing the new pumps.

I came downstairs to find Mimi dressed in her black lace A-line dress. The last time I saw her in the dress, she had added red accessories; belt, pumps, and choker. This time she toned it down a bit and wore a simple shiny black belt and black pumps. We complimented each other and Mimi said my dressing was perfect.


I wasn‘t as nervous as I thought I‘d be when Melanie arrived. She was wearing a nicely tailored dove gray suit; below the knee slim skirt and fitted jacket, with a lovely cranberry red cashmere turtleneck sweater, hand-painted silk charmeuse scarf, and gold jewelry. I greeted her warmly, telling her how nice she looked, and how delighted I was that she could come for dinner. She looked me up and down and shook her head in mock disbelief, laughing as she said "You‘re so damn pretty, Evelyn. It should tick us girls off, but you know, I can‘t help but be glad for you."

We had a great evening. Mimi preferred serving dinner with several distinct courses — the ’French way‘ she said. We started with wine and cheese, then fruits and salads, then the main course of meat and starch, followed more cheese and fruit. We laughed and laughed at Melanie‘s stories. Mimi had a few stories of her own about growing up in Paris. She had one story about a boyfriend who cheated on her and what she did to him for revenge — he ended up broke and in jail. "The bastard didn‘t have a chance, did he?" roared Melanie when Mimi finished her story. I was surprised at how vindictive Mimi was — this was not a woman to be crossed.

At one point, Melanie saw the framed photographs of me on the piano — I had meant to hide them before she came over but totally forgot. I watched as she held the photo of me in dressed in mother‘s black velvet gown and asking incredulously "Is this you, Evelyn?"

Mimi jumped in and said that indeed, it was me, and that she took the photograph. That led the conversation to Mimi‘s photography hobby and, thankfully, away from me.

During the main course, Melanie asked if I was still planning on dressing up for work on Tuesday.

"Oh, most definitely" Mimi answered for me. "I mean, it‘s Halloween and all, so Evelyn has a perfect ready-made excuse in case someone shows up" she added.

"Like that nice teacher of yours… what‘s her name?" asked Melanie.

"Ms. Hunter" I answered.

"Right — in case Ms. Hunter shows up again" continued Melanie.


It was almost ten o‘clock when Melanie left. "I had a wonderful time" she said.

"We‘ll have you over again soon" replied Mimi.

I helped Mimi with the last of the dishes. It was the end of the evening and Mimi said she was heading to bed, tacitly acknowledging that she wouldn‘t be visiting me and tucking me in.

"I‘ll be here all day tomorrow, Evelyn. I‘ve got a nice day planned for you." she said as she reached out and gave my hair a gentle stroke. "Remember our little discussion about how little girls get to have frou-frou days? Hmm?"

My eyes widened as I remembered her telling me that I should have a frou-frou day, a day when little girls got to, as she had described it, "…dress up in their mommies‘ frilliest and laciest things."

My hand went to my mouth and I instinctively bit my fingernail as I softly gasped "Oh."

Mimi just smiled and said "I‘ll come wake you in the morning with some tea and we can start the day sharing our little secret" she said, her eyes fixated on mine. "Would you like that?"

"Yes, nanny" I replied in a blushing whisper, looking down.


I undressed slowly, thinking about the morrow and what fancies my nanny had in store for me. I donned my silk charmeuse set— chemise, tap pantie, pajama bottoms — and the requisite couche-culottes, and then snuggled into bed.


To be continued…

The Awakening of Evelyn - Book 6

Author: 

  • Evelyn D. Fairechild

Audience Rating: 

  • Adult Oriented (r21/a)

Publication: 

  • Novel Chapter

Genre: 

  • Crossdressing

Character Age: 

  • Teenage or High School

Permission: 

  • Posted by author(s)

The Awakening of Evelyn

Book 6

Evelyn D. Fairechild


Evelyn has a frou-frou day with his nanny


Chapter Seventeen — Frou-frou day

Saturday

I woke when I heard Mimi stirring downstairs. It was a gray cold day outside. I had barely gathered my thoughts when I heard Mimi coming up the stairs, calling my name. I rose and opened the door a bit then snuggled back into bed.

Mimi arrived carrying a tray with a pot of tea, scones, cheese, and fruit. She was wearing her blue robe. I was hoping she‘d wear something more intimate.

"Good morning, dear" she said cheerfully as she set the tray down and poured me a cup of tea. "I‘ll be back in a few minutes; give you a chance to wake up and let me change" she said in a soft pleasant voice, adding "…and don‘t forget; it‘s frou-frou day for you."

Anticipating our morning melodrama, I got out of bed, donned my robe, and had a few bites of the breakfast Mimi had thoughtfully brought. I sat at my vanity and primped for several minutes, brushing out my hair, putting on a bit of makeup, and dabbing on some perfume. Back in bed, I fluffed and arranged the pillows so that I could sit upright comfortably and sipped the tea. Soon, I was passing pleasant little streams into my already damp couche-culottes.

Mimi arrived, now wearing her black lace negligee and marabou trimmed chiffon robe. She had spent a little time grooming herself as well — her hair was brushed and she had applied a bit of makeup as well. She stood by the side of the bed and lifted the covers, saying that her feet were cold and asking if it would be alright if she put them under the covers.

"Of course, nanny" I lisped.

She got into bed with me, tucking her feet under the covers and turning towards me. Without a word, she untied the sash to her robe and let it fall open, stretched her right arm on the pillow behind my head, and adjusted the bedcovers around me. She fondled the hair around my ear for a bit and then softly asked: "So… tell me dear… did you have bedwetting problems last night?"

"Uh-huh" I lisped.

And so began our own little secret melodrama of my bedwetting. I was her poor, poor thing, having to deal with issues of bedwetting: the shame and the feelings of inadequacy. I tearfully bewailed that I was a bedwetting sissy. She drew me close, my head resting between her breasts, comforting me, promising to keep our secret, telling me that I was so much better suited to being a pretty young lady. Eventually, I had quite the need to pass water. A shiver went through me. Mimi sensed it.

"Are you alright, mon chéri?" she asked concernedly.

"Oh nanny — I have to go" I moaned.

And just as she had done the previous morning, she said she didn‘t want me leave the bed, that we were comfortable, that perhaps my couche-culottes could hold a little more. She gently stroked the nape of my neck, telling me to relax. With a gasp and a moan, I let go. She adjusted her position to face me better, to watch me as I wetted my couch-culottes. I, too, adjusted my position, rising up, straightening my back, sitting up on my knees.

"Oh nanny…" I moaned. "I‘m… I‘m wetting myself…"

"It‘s alright, mon chéri… perhaps we should look?"

I took her cue and slowly pulled the streamers of my robe sash, untying it, and let my robe part. She reached out and clasped the lapels of my robe and parted it fully, letting it fall off my shoulders.

"Off with your pajamas, Evelyn dear" she instructed.

I took the waistline of the pajama bottoms and slide them down to my knees.

"Oh nanny… I‘m… I‘m still going, nanny" I whispered, looking down at my silk charmeuse tap panties as I placed my hands flat upon each hip.

"Shh… it‘s alright, Evelyn, it‘s alright" she said as she stroked my shoulder. "Perhaps I should check, dear" she whispered as she began to finger the hemline of my panties. "Are you still passing water, dear?" she asked as she felt the two stocking suspenders in front.

"Uh-huh… I‘m all wet now, nanny… I don‘t want to wet my panties, nanny…" I lisped.

"Off with your panties then dear" she whispered.

I slowly drew the tap panties down to reveal the plastic panties.

"Now bend over and I‘ll check you" she instructed.

I bent over, my elbows on the bed, my derriá¨re elevated. She reached between my legs and applied pressure to the pad with her two fingers. I let out a quivering "ohhh…"

"Oh my, Evelyn…" she whispered "…you are quite wet, aren‘t you?"

"Uh-huh" I whined.

"Are you still passing water dear?"

"Uh-huh… a little bit…"

"Well, I think we should take off your pajamas and panties and then you should go downstairs before there‘s any leakage" she said, adding "Tsk, tsk — it‘s too bad that you have to leave so soon. Which reminds me; I do hope the new couche-culottes and things I ordered come soon — they should hold quite a bit more."

I remained in my kneeling position as she helped me out of the pajama bottoms, one leg at a time, then followed with the tap panties. On her cue, I sat up and she removed my robe, and I carefully got out of bed. My couche-culottes were quite sodden, and I thought I felt a trickle escape. Mimi left the bed as well and went to my bureau drawer to retrieve a fresh pair of the terrycloth panties, handing them to me along with my plush terry bathrobe.

"Go on downstairs, dear, and clean up. I‘ll make your bed and start your bath."

I made my way down the stairs, my inner thighs becoming wet due to leakage. In the laundry room, I stripped, rinsed out the couche-culottes and put them the washing machine. I sponged myself off and donned the fresh terrycloth panties — it felt so nice to be dry and snug again. By the time I made it back upstairs, I had to conceal my stimulated daintie with the folds of my bathrobe.


Mimi was standing by my bureau. My foundation drawer was open and she was folding a pair of my panties on the top of the bureau. The bed was made and there was water running in the bathtub. Her black robe was draped across the loveseat as she had donned her blue checked jersey robe.

"I‘ve got a nice bubble bath going for you dear. Why don‘t you slip into the tub and I‘ll come wash your hair?"

"But…" I stammered, suddenly aware that I would be naked in the bathtub.

She chuckled and replied "I know you‘re little ’Miss Modesty‘… just leave on your couche-culottes" referring to the terrycloth panties. "After all, they‘re meant to be wet."

She followed me into the bathroom and helped me out of my bathrobe. The bathtub was brimming with bubbles and I slipped in quickly, not wanting her to see my telltale panties. The showerhead was removable and she took it off its mount to rinse my hair as I leaned over. She sat down on the side of the tub, applied shampoo, and massaged it in, taking five or so minutes.

"So, after we get you all nice and squeaky clean," she began, "I want you to curl your hair to make it as girlish as you can. After all, today you‘re a little girl dressing up in her mommy‘s things. Do your makeup and powdering, and put on your pearls, then come into your mommy‘s room."

She rinsed and lathered me up again, rinsed, and applied conditioner. Then she took my loofah and scrubbed my back for me. She left me to finish bathing, telling me that she‘d fetch mother‘s heated curler set for me and plug them in. I finished bathing and left the terrycloth panties to dry on the towel rack.


I sat down at my vanity and began with my hair in makeup. I took my time getting my hair and makeup just right — I didn‘t want to disappoint Mimi, but I also wanted to join her in my mother‘s bedroom and see what she had in store for me. I couldn‘t resist taking a little of my hashish after doing the details of my makeup. The phone rang while I was in the middle of my grooming. Mimi picked it up in mother‘s room.


Full of anticipation, I made my way down the hall, dressed only in the terrycloth bathrobe. The door was ajar. I could hear Mimi talking on the phone.

I stepped into the room. On mother‘s bed was a shimmering display of silk, satin, and lace, everything laid out just so. I spotted my two petticoats — the princess petticoat that came with the taffeta skirt, and the white petticoat with the double layer of tulle lace netting at the hem. There was the fancifully embroidered pink satin peplum waist combing jacket, the profuse lace chemise that went with my poet‘s blouse, an antique white crotched lace cap sleeve cardigan that I‘d forgotten my mother had, and a white double layer chiffon full-circle skirt of my mothers. There were scarves aplenty — mostly lace and chiffon in whites and subtle pink shades, but there were the long scarves that Mimi had used to tie me up in my princess petticoat in order to dress me in the taffeta skirt. Then more things: a foundation set of my mother‘s, a naughty set, pink with white scalloped lace — bikini, high-cut French briefs, brassiere, and garter belt; a pair of pink silk charmeuse tap panties with an embroidered rose; a full white silk satin vintage dance pantie; a pair of my white silk stockings; and a pair of white lace gloves with a chiffon pouf corsage at the wrist.


Mimi had changed out of her robe and negligee. She was now wearing her new dusty pink cashmere robe, opened to reveal her pink with ornate black lace foundations matched with a pair of nude stockings. Draped across the chair in the corner was her drop-waist pink silk Peau de Soie gown. I guessed that she was going to slip into it, but was interrupted by the phone call.

She smiled broadly at me as she listened to the phone. She whispered "It‘s your mommy, dear."

’Wow‘ I thought to myself; she had been on the phone with my mother for a long time.


She handed me the bikini pantie and motioned for me to put it on before turning her back. I slipped into them beneath my bathrobe. When I looked around, she was handing me the high-cut briefs and nodding to me to put them on as well. I slipped into these dainties and Mimi motioned for me to take off my bathrobe. Then she said into the phone "Here she is… I‘ll put her on"

I greeted my mother as Mimi lifted the brassiere from the bed. Mimi slipped the brassiere up one of my arms to the shoulder. I transferred the phone to my other ear and she completed bring the brassiere to my chest. Because of the time delay, I was able to switch the phone from one ear to the other without disrupting our conversation.

Mother was in Lake Cumo Italy. We first spoke about the packages she had sent from London; they hadn‘t arrived, but mother thought they should arrive early the next week. She was telling me a bit about the region as Mimi moved behind me and fastened the brassiere in the back.

"Mimi says that you two are having a very nice time together and that you‘re beginning to get over you inhibitions. I‘m so glad. She says that Melanie came over for dinner and that you wore that new dress…"

We spoke for a minute or so about Melanie and just how wonderful she was to accept me.

Mimi had retrieved my brassiere sachets from the bed and gently inserted them into my brassiere cups. She was now dealing with my garter belt, fastening it around my waist.


"Did you know that Lake Cumo is one of the world‘s premier silk manufacturing areas? Oh my, but the fabrics here are just exquisite. I‘ve already bought a few things for you and me, but I‘ve got a big shopping day planned."

Mimi motioned for me to sit at mother‘s vanity then lifted a stocking from the bed and, standing beside me, began rolling it in preparation. I looked at the framed photograph mother had taken of me.

Mimi motioned for me to extend my leg. She sat on the tuffet and began rolling the stocking up my leg.


"Did you like that dress you wore for dinner dear? Mimi and I agreed that we‘d we should wait giving it to you…"

"Oh yes, mommy. It‘s a beautiful dress. I really like it…" I replied as Mimi reached the top of my thigh. She then reached beneath the French briefs and pulled the stocking suspender down and began fastening it to my stocking. The eroticism of what was happening to me was offset by the fact I was conversing with my mother. Mimi fetched the other suspender; I had to roll onto one cheek so that she could find the suspender.


"Mimi says she‘s got a special day planned for you" mother said, her voice dropping pitch. "She told me a bit about it. Are you in my boudoir with Mimi, dear?"

"Uh huh" I replied, suddenly confused, wondering how much Mimi had told her about our frou-frou day.

"That‘s so sweet — dressing you up in some of my things. I wish I was there. Tell me, what has she picked out for you?"

Mimi was now rolling up the other stocking. I had difficulty even thinking of what to say — I didn‘t want to tell her everything — it was just so shameful. So I began by telling her about the chiffon circle skirt and the peplum waist combing jacket.

"Oh how fun!" she replied as Mimi was reaching up for the next stocking suspender. "What else dear? Tell me."

I lied about the chemise, not wanting to tell her about the ensemble Auntie sent and the beautiful chemise. Instead, I told her Mimi had selected the Jane Woolrich chemise.

"Uh huh" she replied, waiting for me to tell her more.

"Oh, uh, the petticoat that goes with the blue gown, mommy, and some scarves and things like that…" I practically moaned as Mimi fumbled around beneath my panties for the last stocking suspender.

"And are you having fun dear? Isn‘t it fun to dress up all frou-frou?"

Mimi must have told her about our ’frou-frou day‘ since mother hadn‘t used those words before.

"Oh yes, mommy. Frou-frou is fun" I replied gaily. Mimi looked up and gave me a big smile.


Mimi was now approaching me holding the pink silk charmeuse tap panties. I watched as she opened the panties to place them over my feet and draw them up my leg, and was a bit horrified to see how telltale my panties were and the small wet spot on the front. Mimi saw it too, and stopped.

"Don‘t worry — we‘ll wash your mommy‘s panties later" whispered Mimi, adding "I have an idea though…" motioning towards the small wet spot. She laid the tap panties across my leg, then went to my mother‘s pantie drawer and opened it. She searched through the drawer, taking various panties out putting them on top of the bureau.

"Well, we should plan on having our own frou-frou days when I get back" continued mother as I watched Mimi go through mother‘s panties. "I‘ll keep my eye out for frou-frou. I bet we could find a cute debutant gown or two at that boutique in town — you know, the one where I bought you that pretty pink chiffon dress I caught you drooling over."

I had to chuckle — yes, I was drooling over it. The thought of more frou-frou days like this was thrilling. For a moment, I thought about both my mommy and my nanny dressing me in petticoats and a cute debutant gown.


Mimi had chosen two more panties for me; a shimmering pink satin jacquard French-cut brief and a white charmeuse tap pantie with chevrons of ecru lace on sides. She came over to me and took the tap pantie that was draped across my legs and put them on the vanity along with the white tap panties. "Some extra layers for protection" she whispered as she sat on the tuffet and slid the French-cut pantie briefs over my stocking‘d feet then slowly and seductively brought the panties above my knee to mid-thigh, leaving them there.


"I‘ve got some really wonderful news, dear" mother said as I watched Mimi go through mommy‘s panties. "Your stepfather is probably going to go the Orient on business for three or so weeks after Christmas. You know what this means, don‘t you? You‘ll be out of school and can dress up all the time and I can help you polish up to get you ready to go out."

Mimi had me hand her the white tap panties. She drew these up my legs to just below the shimmering silk jacquard panties.

"And then dear, I think we should all go to New York City and stay at a nice hotel for a week or so. We can have our own special Christmas. It will be your debut."

I handed Mimi the pink silk tap panties. She drew these up my legs.

"I‘ve invited Mimi to come with us, too. After all, she should be there for you debut as a girl."

Mimi went back to the bed to retrieve the vintage dance pantie and was drawing it up my legs. It dawned on me that I would be wearing six panties, each one a perfect overlay of the one beneath.

"We‘ll have a wonderful time. We can go shopping and start to fill out your wardrobe. And there will be all sorts of opportunities for you to dress nicely. We can take in the museums, opera, Broadway plays…"


Mimi had finished with the dance pantie, and she had me stand facing the vanity mirror as she stood behind me. She clasped the waist of the uppermost pantie and slowly brought it to my waist, letting the elastic waistband press settle against my daintie for a long moment.

"We‘ll go see some Broadway plays and go the Met for an opera — you can wear my black velvet gown if you like, or, better yet, we‘ll go out and buy you lovely new gowns to wear. Doesn‘t that sound wonderful dear? I‘m so looking forward to it."

Mimi couldn‘t see my reflection in the mirror as I mouthed an ’Oh‘.

"Oh yes, mommy. Do you think I‘ll be ready?"

Mimi brought the next pantie up, again letting the elastic waistband compress my daintie.

"Oh, don‘t worry dear. Between Mimi and me, you‘ll be perfect… a lovely young lady."

The pink silk tap pantie was next.

"We‘ll have a shopping spree. I know some wonderful boutiques where you‘ll be treated like royalty."

Finally, the vintage white dance pantie was drawn up to my waist.

"And it will be fun to have Mimi along to, don‘t you think?"


The chemise came next. I had to juggle the phone. Mimi fitted me into the chemise and smoothed it out.

Now I was sitting down at the vanity again, Mimi ready with the first petticoat, dangling it in front ~of me.

"Mimi says you helped her buy a new camera and she promised to take some pictures of you."

Mimi started drawing the petticoat up my legs.

"She said you two went out to lunch at that dairy she likes so much. Good for you. I don‘t want you to fret about going out unless you‘re absolutely comfortable. I‘ve discussed this with Mimi and she knows not to force you into going out. It‘ll take time, dear. We‘ll make sure you‘re ready for you debut after Christmas."


Now I was standing as Mimi finished drawing on my petticoat. She went to the bed and fluffed the pillows, cleared off an area, draping the chiffon skirt and princess petticoat over the corner chair. Then she positioned the long scarves and beckoned to me with her finger. I knew immediately what was in store — she was going to bind my legs as she had done before — bind them to make it easier to slide the princess petticoat over the tulle net petticoat I was wearing. Given that there were more long scarves, I suspected she planned to wrap the princess petticoat when done to aid dressing me in the chiffon skirt.

I lay down. Mimi began to bind me — a scarf at the ankle, one just below the knee and one just above.


"Well, dear, I guess I should be going now" she said over the phone, her voice dropping. "I‘m so glad that you‘ve let Mimi help you and I just can‘t wait to see you, darling. Do have a fun frou-frou day today, alright? What a wonderful idea of Mimi‘s. We‘ll have more. But before I go, I just want to tell you that Mimi and I discussed some things about us three. I think it best that she tell you about them."


Mimi was drawing the princess petticoat up my bound legs as I said my goodbyes. She drew it up just below my daintie. She sat down next to me, leaning across me.

"I thought you should wear extra panties to protect from wetness" she said gently. "I guess I should have gotten one of your napkins, but it slipped my mind. But this works too. You can wash them all later. So tell me… you had a nice chat with your mommy, no?"

"Uh huh" I breathed.

"I sure hope your stepfather leaves after Christmas and the three of us get to go to the city. What a perfect time for your debut, don‘t you think?"

"Uh huh" I lisped.

"Evelyn, dear, there‘s something your mommy wants me to discuss with you. But I think before I tell you, I should get you a wrap to keep the chill off your shoulders — perhaps that fur wrap — and a bit of sherry. I‘ll be back in a few."

She disappeared for a minute, coming back with the white fox stole and the monogrammed bolster pillow from my bed. She helped me sit up and arranged it around my shoulders, then put the pillow behind me to help me sit up more. She disappeared again and it was quite a while before she came back. I lay motionless, bound by the scarves. She came back in with the silver tray with the sherry decanter and glasses and set it down on the vanity, then closed the door — unusual since the house was empty. Then she locked it. What was she planning? I thought. She picked up the tray and brought it to the bedside table and poured us each a sherry. She watched me as I sipped, leaning over me, her breasts level with my eyes.


"Evelyn? I don‘t know how to begin, so I‘ll just come out and say it." She paused for effect.

"After you move up to that big house in the Hamptons, your mommy is going to divorce your stepfather"

"What?"

"I hate to be the one to tell you this, dear. You see, your stepfather has been cheating on your mommy. She hired a detective and it‘s all cut-and-dried — your stepfather doesn‘t stand a chance in court. But she wants to go through with the move first before he‘s served with the papers — legal technicalities and all."

"The bastard…" was all I could think of to say.

"Yes, he is. And there‘s no doubt that the settlement will be quite handsome. You and your mommy will be extremely well off."

She let that thought settle in.

"But the two of you will be all alone in that mansion up there. It‘ll be difficult for you at first since you don‘t know anybody up there. And that brings me to the next thing… Your mommy wants me to move in with you two."

She let it sink in.

"I‘d really like to, Evelyn. I‘d really like to move in with you and your mommy. I so want to help and support you and your mommy. I want to be close to both of you. And… well… I think you know what an opportunity it is for you… you can start over… you can be that precious and beautiful daughter your mommy wants you to be. "

"Oh, nanny…" I moaned. It was all coming true — what she told Melanie — I would live as a girl when I moved.

"And I‘ll be there to help you dear… to help you and your mommy. Think about it my dear — three ladies living together. I‘ll be there for you, for your mommy…" she whispered, reaching out and fondling my hair.


My thoughts tumbled from one thing to another. My stepfather — well, I wasn‘t surprised and he meant so little to me that I didn‘t dwell on it… but Mimi moving in with us? Just what was going on? I felt trapped, smothered… What a few weeks ago was an occasional dalliance had turned into something so much more. Living full-time as a girl? It had been on my mind ever since Mimi mentioned it to Melanie, but now it was turning into reality… And the phone conversation I just had with mother while being so playfully, so erotically dressed by my nanny… going to New York City for my debut… My emotions bounced between euphoria and despondency; euphoria bordering on ecstasy over what my nanny was doing to me, despondency over what I had become — an inadequate crossdressing sissy.

I found myself staring blankly at Mimi. I moaned.

"You poor thing, you… I‘m so, so sorry… this is quite an emotional shock for you…"

I moaned again.

"But look at you dear — you‘re all dressed up in your mommy‘s things. Just like a little girl. You do like dressing up all nice and pretty, don‘t you? Wouldn‘t you like to start all over? Start over in a new place as a girl, dressing up all the time?"

"Ewww…" I whined. "Oh nanny… it‘s so sudden. Its wrong nanny — it‘s… Oh nanny…" I was beginning to cry.

"Now dear; we‘ve been over this, haven‘t we? You‘re so much better suited to be a girl. When you‘re all dressed up as a girl, you don‘t have to think about your inadequacies as a boy. You poor sweet thing… you just don‘t know what a beautiful, sensitive, exquisite young lady you are, do you? You‘re so elegant, so demure, so innocent…."

"Oh… oh no" I whimpered, my voice cracking. My whimper was followed with a quiet moan and a titch. Even I wasn‘t sure whether I was crying from my emotions or titching with pleasure.

"Now, now, my poor darling… mon chéri…" she said as she stroked my arm "…it‘s okay to cry — there‘s no one here but us two." She had taken my little moans and titches as sniffling back tears. "Your mommy will be so much happier to have your stepfather out of her life. She‘ll be able to focus her attentions on you, and helping you become the perfect little lady. Just think of it dear… you, your mother, and me, all under one roof, all in that big empty mansion; both of us helping you come to terms with being a lady. In fact, all your boy clothes will be thrown away."

Again I moaned and titched.

"There there, mon chéri: I know just what you need to settle your thoughts… you need me to put your skirt on and finish dressing you, don‘t you? But first, let‘s finish drawing this petticoat all the way up."

In order to bring the waistline of the petticoat to my waist, she removed the bolster from behind my back so that I lay almost flat and then had me arch my back and thrust my pelvis up off the bed. She brought the petticoat up just an inch or two and whispered "relax". I settled back down on the bed, fondling my hair, staring off into space. It took five or six tries before the petticoat was brought to my waist. Each time I arched my back and raised my pelvis, I let out an "uhh…" as if I was straining. She‘d move the waistline up, inching it up my stimulated daintie. She didn‘t acknowledge my aroused state; perhaps she didn‘t notice, perhaps it was because I was willing myself not to become fully aroused, or perhaps that was her intent.


"I need to tie a few scarves around your legs to get the skirt up."

"Oh nanny" I titched.

"There, there; it‘s alright dear… it‘s alright to cry if you need to." Now I wasn‘t sure if she meant a cry of hurt emotion or a cry of pleasure.

She tied the first scarf. "Is it too tight dear?"

"Nooo…"

She tied the second scarf around my knees.

"Ohh…"

"You poor sweet thing… So many things you have to deal with… so many issues…" She was standing over me now, holding the chiffon skirt.

She drew the chiffon up my legs as I let out quiet little moans, little gasps, trying to make it sound like I was holding back tears rather than letting go with pleasure. I was so stimulated, my daintie was surely telling the tale; but my nanny didn‘t say anything.


She offered me her hand, helping me out of my prone position. She had me stand by the side of the bed facing the cheval mirror. I rose and stood carefully, not resisting the scarves tied about my legs. She sat on the bed behind me and brought the skirt to my waist, then had me hold the skirt as she tucked in the chemise.

"There, you‘re doing fine, mon chéri, just fine" she said as she drew the zipper closed.

A belt was next; a wide braided elastic cord woven of pastel scarves, fastened in the back with a hooked buckle. She stood up behind me and took off the mink stole. She was so close to me — I could feel her breasts against my shoulders. She helped me into the crocheted lace cardigan. I buttoned the bottom few buttons of the cardigan and took in my reflection.

"Ohhh…" I sighed.

"See? That‘s what my pretty little girl needed; to finish with her dressing."

The peplum waist combing jacket came next. I fastened the single button at the waist and again took in my reflection.

"Oh nanny — I‘m… I‘m so dressed" I blurted.

"But of course you are, dear; that‘s what a frou-frou day is all about — getting all dressed up" she smiled as she handed me the lace gloves.


"Now, let‘s sit you down at the vanity and we‘ll find you some high heels and finish you up."

"But nanny — I‘m… I‘m still tied up" I whined.

"Oh! Of course — I forgot, darling" she chuckled. "Here, sit down and raise your skirt."

She moved in front of me and gave me her hand for balance. I sat down and began to pull the skirt up.

"Slowly, dear; you don‘t want to wrinkle your mommy‘s pretty skirt" she murmured.

"Yes, nanny" I moaned.

She bent down and untied the two scarves.

"Now raise your petticoat… slowly"

"Yes nanny" I whispered.

"I think my idea of using scarves on you is a good one, don‘t you think? It really helps dressing you when you‘re wearing long petticoats and skirts."

"Yes nanny; it really works well" I offered.

"You like wearing long petticoats and skirts, don‘t you?"

"Yes nanny" I titched.


She slowly untied the three scarves. She took two of them, a cream lace and a peach charmeuse that closely matched the combing jacket and drew them through her hand, matching the lengths, and then tying them together to form one very long scarf. "Let‘s use these as a neck scarf" she said, looping it around my neck, pulling my hair out and over them. Then she tied the scarves on the side of my neck, leaving one long streamer and one short.


In a daze, I was led to the vanity where she fastened the pink chiffon hair bow into my hair. She opened the closet and searched around for shoes, coming up with a pair of white satin pumps that I remembered my mother wearing to a wedding. She sat on the tuffet and helped me into them.

"Stand up dear, and let‘s have a look at you" she whispered with a smile.

She stood beside me in front of the cheval mirror.

"Just look at you!" she exclaimed. "All dressed up in your mommy‘s things, just like a little girl."

We stood silently for a long minute, Mimi fussing a bit with my jacket and scarf and hair.


"Now, can you zip me up?" she asked, motioning to her dress draped across the chair.

"Yes, nanny… of course" I replied.

She slowly took off her robe and tossed it on the bed. "Do you like this set?" she asked coyly, placing her hands under her breasts then smoothing them down her torso.

"Oh, yes nanny" I sighed.

"I think I should buy some more sets like this. Just for you."

She stepped into her dress. I helped a bit then zipped her up.

"You‘re so sweet. Can you help me with my heels?"

There was a pair of red ankle strap heels beneath the chair. Mimi sashayed over to the vanity and sat down. Now it was my turn to sit on the tuffet. She put her foot in my lap and wiggled her toes. I lifted her foot and began putting on her shoe.

"Ummm… It‘s so nice having you do this for me" she whispered.

I fumbled with the buckle of the strap and eventually fastened it. She was humming to herself. I started with the other shoe. She coyly bit her fingernail.

"Ummm… that‘s right, darling…"


She turned to the vanity mirror and applied deep red lipstick while I sat and watched.

"Let‘s go downstairs and take a few photos, okay?" she said when she was done. "Come along dear" she said, taking the scarf streamer from around my neck and standing up. She didn‘t let go, but led me to the door and opened it.

"Come along now" she said with a smile, still holding the scarf streamer as she led me down the hallway, my petticoats rustling. She let go of the scarf steamer when we reached the top of the stairs.


We stayed downstairs for an hour or so. She took some photos of me by the piano and sitting in our regency silk upholstered wingback chair. She set up the tripod and took a few of us together, standing behind and to the side of me, her hands on my shoulders. Then we ate some finger sandwiches and had a little more sherry. She made sure I had my vitamins.

I had to go to the bathroom which turned out to be quite a little adventure. Mimi showed me a trick — I could take the scarf from around my neck and after lifting my skirts and petticoats, tie the scarf around my waist to hold everything up while I drew down my panties and sat. It worked to some degree. I drew my panties down to my ankles one at a time, except for the bikini panties which were beneath the stocking suspenders. It took me quite a while.

We had one more glass of sherry and Mimi said "It‘s time for your nap, dear. Let me go upstairs and turn down your bed for you. I‘ll call you when I‘m done." She left, taking her camera with her.

I evaluated myself in the mirror in our formal living room and waited for Mimi‘s call.

"Evelyn dear? It‘s time for you to come to bed" I heard her say from the top of the stairs. I went to the foot of the stairs. She was standing at the top and watched me as I lifted my skirt and petticoats and gingerly walked up. She took the streamer of my neck scarf and led me to my boudoir.

She had turned down the bed. The turned-down covers revealed my big pillow with my monogrammed initials. Hanging on scented hangers from the dressing screen was my mother‘s diaphanous pink nightgown and robe. Mimi walked over to the mirror and took the negligee off, holding it up. "Since you‘re dressing in mommy‘s things today, I thought you might like to wear this. It‘s so pretty."

Music was playing — it was the ’Private Dancing‘ CD that she had bought me. I noticed that her peach cashmere robe was draped across one of the chairs, and that a pair of couche-culottes with pink plastic panties was on the loveseat.

"First things first, dear; could you unzip me? I‘d like you to help me out of my dress before I go take a nap in your mommy‘s room."

I unzipped her and she stepped out of the dress, picking it up and putting it on the wingback chair, then donning her peach cashmere robe.

"Now let‘s take a picture of you standing by your bed" she said. She had me pose by the bed post, leaning against it, holding my hand mirror up and admiring my reflection.

"Now… a few of me, alright?" She went to the other side of the bed and kneeled on one knee in front of the pillow. She let her robe fall from her shoulders. Then she plucked the open end of the pillowcase, picking it up between her fingers to show its lace to the camera.

"Oh nanny" I whispered, blushing deeply. She smiled at me. As I held the camera up to take the picture, she put her other hand on her breast and pouted her lips. She had me take a couple of pictures.

"Now, dear, come sit with me for a minute" she said, coming around to the other side of the bed and curling her legs beneath her, patting the covers next to her. I sat down. She put a hand on my thigh.

"Dear? I‘m thinking that you want to undress in private, no?"

"Uh huh" I moaned.

"That‘s what I thought. Now… I want you to have a nice nap, alright? Don‘t worry about a thing. Clear you thoughts dear. And don‘t worry about your mommy‘s panties — we‘ll wash them after your nap, alright?"

In a rasping lisping voice I replied "Okay… uh…" followed by a titch.

She kissed me on the cheek and rose from the bed, closing the door behind her. She had left her dress on the chair.


I drew back the covers and nestled onto the pillow, lifting the chiffon skirt and two petticoats, and began to stir ever so slowly. All I could think of was that I was going to cream in my mommy‘s panties — my nanny said it was alright. I took three long languorous churns, letting out a gasp on each one, then paused, taking in shallow little breaths, breathless little O‘s escaping. Then another three, then another… I roiled in my luscious agony. I couldn‘t believe how erotic my nanny was becoming. I was completely, utterly, hopelessly under her spell. I didn‘t care if she heard me. If she was listening, there was little doubt she would. As the moment arrived I lifted myself off the pillow, holding my skirt and petticoats up so I could see my layers of panties in the mirror. Oh how I cried out as I watched myself in the mirror, creaming into my mommy‘s panties.


Mimi knocked a couple of hours later. I had changed into the couche-culottes and my mother‘s pink nightgown and robe. My mother‘s panties, completely soiled with my cream, were soaking in the sink. The rest of my frou-frou dressing was scattered about the room. She entered carrying a tea tray, wearing her pink cashmere robe, tightly tied around her.

"Good afternoon, dear. I brought you some tea" she said pleasantly.

She poured me a cup and sat on the bed. I sat up and sipped the tea. It was her special blend.

"Did you have a nice nap?" she asked, brushing my hair aside with her finger.

"Oh my, nanny; it was very nice" I replied.

"I thought so" she said with a smile. "So, I think you like your frou-frou day so far, yes?"

"Oh yes, nanny" I replied enthusiastically.

"You look so very lovely in your mommy‘s nightgown. Do you know what would be fun? If you and your mommy wore identical nightgowns every now and then. Perhaps when we all go to the city, you two can go out together and shop for nightgowns and buy a couple of matching ones. Then you could show me later. I‘d like to see that."

I couldn‘t think of anything to say. The thought of my mother and me dressed in matching nightgowns in front of Mimi gave me a chill.

"Are you wearing your couche-culottes?"

"Uh huh"

"Did you have bedwetting problems?"

"A little bit" I whined. In fact, my couche-culottes were dry, but I suspected they would be wet in a bit.

"Well, that‘s to be expected" she said, looking at me fondly.

"Uh huh — I know now to always wear my couche-culottes in bed, nanny. In case I have an accident."

"Good for you. I have a surprise for you" she said, straightening up. "When I was downstairs fixing you tea, the mailman delivered a package for you. It‘s from your aunt. Would you like me to go get it?"

My eyes brightened and I must have let out an audible gasp. My Auntie had sent me more things!

"Oh yes, nanny, could you?" I asked.

"Of course, mon chéri, of course; I‘ll be back in a few."


She came back with the box and a knife to open it.

"Why don‘t you open it while I go change into a nightgown? Do you have any requests for which nightgown I should wear? My new blue one? Or my black one? Or maybe my peach one?"

"Oh nanny" I mumbled. What a question! I couldn‘t think.

"Hmm?" she asked. She opened her robe a bit to show that she was still wearing her pink foundation set. "Or do you want me to wear one of my sets? Hmm? I could put on my black set. Would you like that? Or the white set with the black lace?"

She was waiting for my answer. "Uh — how about your new blue nightgown?" I asked tentatively.

"The blue nightgown it shall be, mon chéri. I‘ll be back and you can show me what your aunt sent you. I bet it‘s a pretty new dress." She left, taking her dress with her.


I opened the box. There was a note on top that read:

My dearest Evelyn:

I thought you could use a cuddly warm sweater set to lounge about the house in, and a new pajama and robe bedtime set for those chilly evenings.

Much love,

Aunt Beverly

Pinned to the note was an oh-so-very-very-soft blush pink draped cowl neck sweater, made of the finest mohair. It had two layers, an inner layer of off-white fine mesh, and then the outer layer of open weave blush pink. It was rather long, with a tight waistband and long raglan sleeves. I let out a squeal of delight as I held it up. I surmised that the tight waistband would allow the extra length of the sweater to fold over the waistband giving the sweater a very clean line.

I let out a sigh of ’Oh my, Auntie‘. Returning to the box, I found a bundle of burgundy red satin tied up in a long red satin ribbon of nearly the same color. I gently lifted the bound garments from the box, put the bundle on the bed, and untied the ribbon. On top was a pair of pajama bottoms. The fabric was a luxurious synthetic satin, quite glossy. The outside seam of each leg was finished with a one-inch wide ribbon of a complementary red satin. I was expecting a pajama top next, but instead I found a chemise. The bodice was a draped square-top, with a half-dozen wide pleats running horizontally across the chest with pink lace netting in between each pleat. The shoulder straps were one-inch wide, the same color as the seam accents on the pajama bottoms, and the hem of the chemise was finished with the same accent ribbon. Next, a pair of culottes, mid-thigh length; the waist adorned with the same pleats as the chemise and the leg hems finished with satin ribbon. Then a full length robe, the quilted lapels and cuffs made of the same complementary satin, as was the wide sash.

I returned to the box, for there were still things in there, hidden beneath a layer of pink tissue paper. I lifted the tissue paper to discover another note from Auntie that read:

Evelyn, sweetheart — just a few more things, just in case you‘re in the mood for dressing up!

Beneath the tissue was a full knee-length skirt of the same ribbed mohair as the tunic sweater. I let out another squeal of delight as I laid the skirt next to the sweater. What a pretty set! Beneath the skirt was a matching full-length nightgown, essentially the same as the chemise, but the bodice had a bit more drape. At the waist on either side were two ribbons that tied together to fit the waistline. Then more treasures — a white crepe chemise, tap pant, and pettislip all adorned with pink lace. The fabric was some sort of synthetic and needed ironing. I surmised it was a vintage set. The chemise had a deep chevron of pink lace at the bodice as did the kick-pleat of the pettislip and the sides of the dance pantie. A foundation set followed; padded full-cup brassiere, garter belt, and French-cut briefs, all white satin with pink lace. This was a new set by Wacoal and closely matched the daywear set. The last delicacy was a pair of white crochet-knot merino wool stockings.


I had just finished laying out the presents and hiding the notes from Auntie when Mimi entered, wearing her powder blue embroidered kimono and empire waist nightgown.

She sat in the chair as I showed her my new treasures, commenting on them, saying things like "oh, that‘s exquisite" and "such beautiful things for a beautiful young lady".

I was standing at the dressing screen mirrors, facing Mimi, holding the nightgown up to me after showing her most everything, when the chill went through me. I could have easily dashed off to the bathroom, but instead I moaned "Oh nanny… I‘m having an accident."

"There, there… it‘s alright, dear. You‘re wearing your couche-culottes" she said reassuringly.

"Oh" I gasped, biting my fingernail as I began to pass water. I minced over to the loveseat and laid the nightgown on it. "Oh nanny" I gasped again as I made my way back into bed. Mimi rose at the same time and joined me in bed. Soon, she was cuddling with me, stroking my hair, my head on her scantily clad breasts, and my fingers on the delicate straps of her nightgown. She comforted me, telling me that she understood my problems. The first wave abated, and Mimi seemed to notice because she released me from her embrace and changed the subject.

"Your aunt certainly knows that you like dressing up, doesn‘t she? That‘s why she keeps sending you such nice things. Come to think of it dear, after you and your mommy visited your aunt this summer — that‘s when your mommy really decided that she wanted you to be her daughter. I think it was something your aunt did that convinced her. Can you think of something your aunt said of did that convinced your mommy?"

"Uh… no" I lied, thinking about how she and Suzanne dressed me. For some reason, I didn‘t want to reveal that to Mimi. I thought she might get jealous or something.

"Have some more tea, dear" she said, pouring another cup.


"Now, here‘s what I think, dear. Tomorrow, I have to deliver some papers to a sweet little old lady who‘s selling her house. Her name is Carol. I think you should come with me and wear your pretty new dress and things. I‘ll introduce you as my friend‘s daughter or my niece. She won‘t have a clue that you‘re not a real girl. How does that sound? It‘ll be good to get you out of the house again."

"Sure — I‘d like that, nanny."

"But I have an idea — I think you should wait until tomorrow before you dress up in your pretty new dress and underthings. It will give you something to look forward too. But you can wear your new nightgown tonight. How does that sound?"

"Oh — okay" I whined, disappointed that I couldn‘t dress up in the oh-so-soft sweater and skirt until the next day. "But I was looking forward to dressing up in it tonight" I added.

"Oh, I‘m sure you‘ll think of something nice to wear; perhaps something of your mommy‘s? After all it‘s a frou-frou day so you can wear anything you want."

"Hmm" I purred, remaining non-committal. I took another few sips of tea. Mimi began to fold the things on the bed and put them on the loveseat. A few minutes passed and I had to go again.

"Nanny? Oh nanny — I…" I moaned.

"Are you wetting yourself again?" she asked with playful derision as she sat down next to me.

"Uh huh" I moaned.

She cradled me again as I let out quiet little O‘s.

"I don‘t want to wet my mommy‘s pretty nightgown" I whined.

"We should check you, then" she whispered in my ear.

A minute later, I was in position, watching in the mirrors as her hand slid between my legs to check for wetness.

"Oh nanny!" I gasped as she pressed her fingers against the pad.

She declared that I was still dry, but that I should go downstairs and change.


When I returned, she was rinsing out mother‘s panties. She had taken off the robe and was just in her nightgown — I figured it was because she didn‘t want to get the sleeves of the robe wet. She had started a bubble bath for me. She wanted to wash me again, just like she had that morning. I complied, putting my hair up in a shower cap and, wearing the terrycloth panties, slipped into the tub. She went and put on her blue checked robe and returned to gently wash me with a washcloth, and then switched over to the loofah to do my legs and feet. I told her how much I appreciated her washing me. She looked at me lovingly and said "maybe next time you‘ll get over your modesty and not wear panties in the bathtub."

When she was done, she told me to be sure to use lots of lotion and powder and to take my time dressing for dinner. "You‘ve had an emotional shock today, Evelyn. I think it would be best for you if you passed the time dressing up rather than thinking about your future. Just think about the now."


When I came into my bedchamber from the bath, I noticed that she had taken away the sweater dress and new underthings. She was serious — she didn‘t want me dressing in them until the next morning.

It took me over two hours to dress. Mimi checked on me a couple of times. I had decided to wear my mother‘s empire waist wool jersey dress in dark blue with a floral pattern — the dress she wore the day she dressed me. I was a perfect day-to-dinner dress and I guessed I liked the symbolism of wearing it. I really paid attention to my hair, makeup, and accessories. But while I was sitting at my vanity, I got an idea about my stash; I should take some of it downstairs so that I could partake between the time Mimi was getting my room ready and when she called me to bed. I could split the stash into two and bring half downstairs with me and into the downstairs bathroom. It had exhaust fan, I had an extra pipe, there was mouthwash in the downstairs bathroom — it could work. So I divided my stash and put half into a plastic baggie which I put into a blue shoulder bag I decided to carry with the dress, along with makeup.


It was dark by the time I descended the staircase all done up in the dress, carrying the shoulder bag with my makeup and contraband. Mimi was wearing her creamy off-white ballet dress with a black lace shawl tied around her waist, a black chiffon neck scarf, and red heels. We complimented each other.

"Why, Evelyn, isn‘t that the dress your mommy wore the day she dressed you up?" she asked.

"Uh — yes it is, I guess. How did you know?"

"Oh, I just know" she responded coyly.

I blushed when she said she was looking forward to undressing me after dinner.

We ate dinner at the dining table with light conversation, not touching on any of the subjects from the morning.

After clearing the dishes, she said softly "Now dear, I‘m going to go upstairs and change and then I‘ll call you. Do you have any requests? Would you like me to wear one of my sets?"

"Um — sure nanny; I‘d like that" I replied honestly.

"I just remembered that I have a set you haven‘t seen yet. I‘ll wear that, okay?"

"Oh — that would be nice, nanny. I can‘t wait to see it" I replied happily.


As soon as she went up the stairs, I went to the bathroom, turned on the fan, and partook. I rinsed with mouthwash and sprayed a bit of air freshener, hid the stash in the corner of the vanity beneath some towels, then turned my attentions to the mirror and freshened my makeup. I left the bathroom, shut off the lights, save for one in the living room, where I studied myself in the big mirror awaited my nanny‘s call, still astonished with how utterly sensual she had been that day, how I was completely under her spell, willing to do anything for her. The call soon came: "Evelyn dear? It‘s time for you to come upstairs and let me put you into your new nightgown."

I shut the light and went to the bottom of the stairs. There was my nanny, standing at the top of the stairs, her black chiffon gown tied around her. I couldn‘t see what was beneath. "Yes nanny, I‘m coming nanny dear" I replied, slowly making my way up the stairs.


She took me by the hand and led me to my boudoir. She had the intimate music playing, the lights down low. My bed was turned down and there was the pillow peeking out from beneath the turned down bed cover and sheets. Hanging on the dressing were the new burgundy red satin gown, mid-thigh length culottes, and the matching robe. On the ottoman in front of mirrored dressing screen was the couche-culottes, pink plastic panties, and the white satin bustier with the white cotton stockings.

She stood in front of me and said "Can I show you my set now?"

Wordlessly, she undid the sash of her robe and opened it, letting it fall from her shoulders, to reveal an oh-so-delightful shimmering silver-gray brocade over-the-bust corset with ruffled ecru tulle trim, a matching brief, and black stockings clasped to the ecru suspenders of the corset. The corset compressed and raised her breasts so that her cleavage was quite pronounced.

"Oh my nanny!" I exclaimed "It‘s so beautiful. You‘re so beautiful."

She ran her hands down her side and drew in a breath. "You‘re so sweet mon chéri. I‘m glad you like it. It‘s something I‘ve had for a while. I‘ll be sure to wear it again for you. Now, let‘s attend to you."

She turned me to face dressing screen and its mirrors and slowly unzipped me. I let out an ’oh nanny‘, making it sound like I was on the verge of crying. I blinked a couple of times, working up tears — something I had always found easy to do.

"There there, mon chéri — you‘re crying, aren‘t you? Go ahead — it‘s good for you" she whispered. I was glad she was mistaking my little moans and sighs and titches as crying rather than what they really were — barely controlled O‘s. She slowly took the sleeves off my arms, having to pause to remove my bracelets. Then she pulled down the dress and helped me step out of it, revealing my blue silk surah chemise and tap pantie. The chemise was next; she gathered the hem and rolled and folded it up past my brassiere then had me raise my arms. Then she drew down my panties. I let out a quivering little moan followed by a sniffle to make my faux crying plausible.

"You poor thing" she whispered. "You‘ve had such an emotional day… all these new things to think about… moving to the Hamptons, your mommy wanting you to dress as a girl all the time… We know you‘re going to be lonely and scared at first, but I‘ll be there to help you…"

She unfastened a stocking and had me put my foot on the ottoman so she could unroll it and take it off.

"Oh nanny" I sniffed. My daintie was all moist and wetting my damask napkin.

"Don‘t worry dear. It will be fine, I promise. Your mommy is going to spoil you with fine things. And you‘ll be going out together and you‘ll eventually make friends. One thing I do know — your mommy and I are going to have a dickens of a time keeping the boys away from you."

I blurted out a moan when she said that. Boys! A chill went through me thinking about them. I wasn‘t ready to deal with boys — not yet, anyway.

Now she was working on my remaining stocking.

"But both your mommy and I know that it‘s going to be so difficult for you, being a boy all dressed up as a girl. No one will ever suspect what‘s beneath your pretty dress and intimates, and we don‘t want them to find out, do we?"

"No, nanny" I whined.

"It has to be our little secret, doesn‘t it? Just between you, me, and your mommy. We don‘t want the neighbors and such finding out that the splendid young lady living in the fine mansion is a boy. Not until we‘re sure they‘d understand, like Melanie. We know it‘s going to be difficult for you. That‘s one of the reasons she wants me to move in. Because your mommy understands that you have certain needs."

"What do you mean, nanny?" I lisped. All I could think of was my frequent creamings, but that couldn‘t possibly be what she meant. Or could it?

"Oh… just certain needs, dear; we‘ll discuss them later this week, alright? All in good time — I don‘t want to upset you now, not after the day you‘ve had. There‘ll be plenty of time next week, mon chéri" she whispered in my ear as she unhooked the garter belt and removed it.

"Okay, nanny" I replied in a high lilting voice.

"I‘m so glad you trust me on these things" she said. Her voice was so soft, so mesmerizing. "It will be wonderful, dear. You‘ll see. Now go put on your couche-culottes. You don‘t want your bedwetting to wet your pretty new nightgown and panties, do you?"

"No nanny" I sniffed, wiping away a tear.

She picked up the couche-culottes, but before handing them to me, she examined them and said "You know, dear, your mommy is going to eventually find out about your bedwetting. Perhaps I should talk to her about it."

I was too high on hashish and too aroused to protest.

"Yes, nanny… P… please tell her I‘m sorry… I‘m so ashamed… to be a bedwetter and all."

"Now, now, don‘t fret. I‘m sure she‘ll understand."


I came out of the bathroom wearing the couche-culottes. I was struck by the fact that days ago I was embarrassed to let Mimi see me without a top on. I was still embarrassed, but after the last few days, I felt less so. She helped me into the robe saying "We can‘t let you become chilled now, can we?"

She wanted me to apply my moisturizing lotions, and watched as I sat at the vanity and massaged the lotion into my arms and legs and chest and used cold cream to remove my makeup.

"I just realized something Evelyn; you can‘t put lotion on your back, can you? How silly of me."

She rose, went to the bed, put the pillow back by the headboard, and drew the sheets and bedcover back over the bed.

"Come, lay down; I‘ll put lotion on your back" she said gaily.

I took off the robe and lay down, not knowing what to expect. I let out a yelp when the cold lotion hit my back. "Wasn‘t expecting that, were you?" she giggled. She began to massage in the lotion.

"Your skin is so very soft, Evelyn" she said. When her hands came to my ribcage, I giggled.

"Ticklish, huh?" she mused. She began to tickle me more.

"Nanny!" I blurted, giggling.

"Oh — so sorry" she replied in a mocking tone. She went back to massaging in the lotion, then tickled me again.

"Nanny — stop!" I laughed.

"Oops — silly me" she said playfully. She waited a moment and then tickled me on the inside of my knee.

"Oooh! Nanny… hah" I laughed.

A minute of massaging and tickling followed and I finally had to sit up to make her stop. We were both laughing. She reached out with both hands and tickled my ribcage again, and I let loose with a most girlish "Ooooh". That just caused her to tickle me some more, walking her fingers up from my abdomen to my chest, eliciting another series of girlish O‘s from me. Then she quickly stood up and smiled down at me.

"Okay, enough shenanigans, Evelyn" she scolded me with a grin, as if it was my fault she was tickling me. "You have to finish dressing for bed, or you‘ll catch a cold."


I rose from the bed and she helped me into the bustier and robe and had me sit while she rolled the stockings up my leg and together we fastened them to the suspenders. We talked about the next day and how I was to dress in the new sweater dress Auntie sent me. "Next week is going to be so much fun. You get to dress up for the library. And there‘s the costume party on Friday. And we can have another frou-frou day, too. Now dear, let‘s put you in your panties and nightgown, and then I‘ll brush your hair."

I was standing in front of my mirrors again as my nanny drew my new culottes up my legs and over my plastic panties then drew the nightgown over my upraised arms, then tied the side-ties which shaped out the nightgown.

"It fits so well" said nanny as I took a turn or two in the mirror.

She helped me back into the robe and guided me to the vanity, turning off all but the bedside lamp and the vanity lamp. She sat behind me on the tuffet and began to brush my hair.

"My poor sweet chéri" she began, dropping her voice as she continued to brush my hair. In between her long languid strokes, she spoke softly and slowly. "Don‘t worry dear; it will all be fine… I feel so sorry for you… you look so sad all the time… I know you‘ve been crying… It‘s all right dear; everything will be fine, especially after we move… You‘ll see… You‘ll like being mommy‘s precious girl… Your mommy and I are going to do everything she can to make sure you‘re happy…"

I sat in my fine new robe, chemise, and culottes, listening to her, taking in the scene reflected by the vanity mirror, and started my faux crying, sniffling and letting out quiet little gasps and titches.

"Tomorrow starts a new week for the new you… I‘ll make sure everything is just right for you… You don‘t have to worry about a thing… I have some things I want to discuss with you and I‘ll set aside some special quiet time for us…"

She put the bush down and wrapped my hair in the long red satin ribbon that was used to wrap the set I was wearing.

"Let me turn your bed down before I leave, mon chéri" she whispered as she stood up. She went to the bed, turned down the sheets, and put the pillow back in place. She came to the vanity and gave me a wet kiss on the cheek, and left.


To be continued…


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