The Awakening of Evelyn - Book 2

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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

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Comments

So, So...

So soft, so delicate, you could dream and be there with Evelyn. The sheer bliss of the moments. Was the special Tea, also helping? With it's special herbs? hmmm... I just love it, Mary

I cannot find any words to describe how I feel about this story

Andrea Lena's picture

...other than what Mary already spoke...sheer bliss...I just love it as well!


She was born for all the wrong reasons but grew up for all the right ones.
Possa Dio riccamente vi benedica, tutto il mio amore, Andrea

  

To be alive is to be vulnerable. Madeleine L'Engle
Love, Andrea Lena

Ah, a special tea and

Ah, a special tea and vitamins. Can you say "girlhood on the horizon"? Evelyn won't even have to change her name. Mom, Auntie, Suzanne and Mimi are all in this "makeover" together regarding Evelyn. I sonehow feel she won't be making it to Berkley any time soon.
Jan

Tea / vitamins

It's practically a trope in TG fiction that whenever the protagonist is unexpectedly put on a course of "vitamins", they usually contain C18H24O2...
I wouldn't be at all surprised if this is the case - especially with Mum's comment that ladieswear seems to fit him better than menswear...

Still, it's an entertaining story, and it'll be interesting to see when Evelynn finally admits he enjoys the dressing up. At the moment, it's pretty much an open secret (he enjoys doing it, everyone else knows he enjoys doing it, but he's not yet ready to publicly admit he enjoys doing it). Meanwhile, I wonder if during the course of Mum's holiday he'll be more daring with his dressing up (esp. at the library), or maybe venture out in public while dressed up...

 
 
--Ben


This space intentionally left blank.

As the right side of the brain controls the left side of the body, then only left-handers are in their right mind!

This is a CD adventure

ALISON

'story but is so soft and feminine and I am still loving it the second time around.Thank you so much Evelyn for a heart warming story.Love and hugs,Alison.

ALISON

Where is reality?

NoraAdrienne's picture

This boy is 18yrs old and his mother is able to use parental controls on the computer to block him? Please.... Where is his drivers license? My son in law is from Philli and I know that he should be driving already..

I'm sorry, I think the story is very soft and cuddly but it's reached the point where suspension of reality no longer works for me. Either he tells him mummy that he's a CLOSET crossdresser or he asks her point blank whether she really wanted a daughter instead of a son.

Love the Librarian

How sweet a story! When I was a teen, my only refuge from the rough world of boys was the library. This was many years ago, before television and video games. I dreamed of being a girl even then, and always looked at the librarians as models. What better place for a shy, rather slender boy with poor eyes! The story may be getting a bit unrealistic due to the long period of time of subterfuge, but,alas, it's fiction... and I love it. Katherine