Part I
I stood for a moment in the bedroom looking down at my stepmother’s nightstand. Phyllis’ dressy bracelet watch gleamed softly in the dim light. As I picked it up and slowly slipped it over my dainty left hand my heart raced, and I sighed a long, shuddering sigh.
Ohmigod, I said to myself as I fumbled with the clasp-and-chain closure. Finally-finally!-I clasped it in place and lowered my hand. The wide, surprisingly heavy brushed gold Seiko slipped down my frail wrist and rested against my hand, and this time my sigh was more of a moan. I held my hand out limp-wristed, admiring the effect in her full-length mirror.
As I gazed appreciatively at the piece of jewelry on my wrist I suddenly noticed, in the vanity mirror, that Phyllis was standing in the doorway.
I froze and stared at her reflection, too stunned to speak. Neither immobile nor mute, she strode into the room and grabbed my shoulder and spun me around. “You little fairy,” she spat out, as she took my hand and removed her watch from my wrist. She absentmindly put it on her own wrist, then stepped back, hands on her hips, and gave me a severe glare as I looked down at the floor.
Since early childhood I have been fascinated with women’s jewelry, especially with certain types of fashionable bracelet watches. I occasionally had the opportunity to try on my older sister’s, before she left for college, but no one had ever known of my fetish. When father remarried a few years later I had just turned twelve, and in the four years since then I had been absolutely fascinated with my new stepmother’s wardrobe and jewelry, but especially with her elegant bracelet watch. And the first time Ihad the chance to try it on I had been caught.
“What else have you been getting into?” Phyllis finally said, looking around the room. “My lingerie? My high heels? Don’t little fairies like you wear lingerie and heels?”
I finally found my voice. “Oh, no,” I squeaked. “This is the only . . . that is, I’ve never-I mean, um, I’m not a fairy . . .” I concluded miserably. She smirked. “Of course not,” she said sarcastically. “But then again I don’t know . . . I’ve always thought you were a bit girlish-and now I find you sneaking around trying on my jewelry. Not a fairy? What would you call yourself, then?”
I hung my head again, but Phyllis stepped forward and lifted my chin with one long-nailed finger. “I asked you a question,” she said evenly. “What would you call yourself?” I gulped and looked her in the eye. “I guess I think of myself as more of a, a sissy,” I said meekly.
She actually smiled. “That’s true,” she said. “You are a sissy. Yes, that’s a good name for you,” she said.
She stepped back and cocked her head. “I’m going to do something I’ve always wanted to do, ever since the wedding,” she said. “You were girlish then, too . . . do you remember the gown that your little cousin Rachel wore? Well, I remember thinking once that you would have looked cute wearing the same thing, instead of that tux we had you in.
“Since then I’ve wonderered several times,” she concluded, “What you would look like as a girl.”
My eyes widened. Being dressed like a girl was my fondest desire, but I was far too embarrassed to admit that to Phyllis, so I said, “What do you mean?”
She didn’t answer, but continued to eye me critically. “You’re so petite, my clothing won’t fit you,” she said, “but my shoes might.” She stepped to her closet and took out a high-heeled pump. “Sit down and take off your shoe and sock,” she said briskly. I did so as she opened a drawer and took out a nylon footie. She slipped that on my foot, then slid on the pump. It was, in fact, a perfect fit. “Good,” she said. She immediately took the shoe off again and put it back in her closet.
“Now stand up,” she said, “and take off your clothes.” I hesitated and looked down shyly, so was caught off guard when she grasped my chin between thumb and forefinger. Her inch-long crimson nails dug into my cheeks, making me gasp. She brought her face close to mine. “When I tell you to do something,” she said, “you will do it-immediately-without question. Is that understood?” I couldn’t speak, so only nodded. She released me. “Good,” she said calmly, “now take off your clothes.”
I obediently (but shakily) stripped myself of my other shoe and sock, then took off my pants and shirt. My cotton briefs had a bulge in them. Phyllis looked at my uncomfortable situation wryly but made no comment. Instead she took out the cloth tape measure she had found and began to take my measurements. She measured my chest, sleeve, waist, hips, inseam, and even my head, jotting down all the figures on a notepad. “All right,” she said. “Get dressed. We’re going shopping.”
Part II
“What do you think of this one?” Phyllis asked, holding up a frothy pink chiffon tea-length gown. “It’s, uh, nice,” I said, trying to act bored. Phyllis gave me a stern look. “Come now. Which one do you like the best?” she asked.
I gulped and looked around again. We had been in the shop for nearly a half hour, and Phyllis had held up at least a dozen beautiful formals for my perusal. The curious looks from passersby had been the source of almost constant embarrassment.
I knew that she wanted an honest answer, though, so after a flustered moment I blurted “The red one,” and immediately blushed. She raised her eyebrows. “Ah, yes,” she said. “I should have known. I’ll go buy it for you-we already know it will fit.”
Two teenage girls standing nearby looked up at that statement and saw me blushing. They looked at each other, then without a word left the shop. I could hear them giggling as they walked out into the mall.
Our saleslady was a bit annoyed at us for driving away customers, but Phyllis handed her an extra few bills with her credit card and she became more friendlier. “Are you sure you don’t need to look at some formal lingerie?” she asked. She smiled sweetly at me and said, “You can use the dressing room, if you like.”
Phyllis said that was a wonderful idea, so the saleslady showed us several styles of bra and panty sets, stockings, and slips. Soon Phyllis was holding my arm and leading me to the back dressing room. I blushed a bright scarlet, nearly matching the armload of lingerie she was carrying.
After going back a couple of times to find a bra that fit me better, Phyllis led me back to the counter, where she bought the lingerie. The shop owner and both of her employees were by now openly giggling at me.
Phyllis made me carry the dress bag as we made out way to the car, and I followed her with relief. At least we were done.
We went out and got in the car, and I stashed our purchases in the back seat. “Our next stop is downtown,” said Phyllis, surprising me out of my reverie.
“Next stop? . . .” I said, confused, but she only smiled and started the car.
We drove downtown and parked at a garage, and I followed Phyllis, mystified. Where could we be headed? When she turned and entered a wig shop I nearly died, but after looking around to see if anyone was looking I followed.
Row upon row of beautiful wigs lined the walls. No one else was there, so the saleslady immediately approached us. “Can I help you?” she asked Phyllis. “Yes,” she answered. “This is rather unusual, I know, but we wish to purchase a wig for my stepson.” The saleslady nodded, and walked to a display of men’s toupŽes. “No, no,” Phyllis said, “I mean we wish to purchase a woman’s wig for him. Something like that long blonde one in the front window.”
The saleslady stopped in her tracks and looked at us without expression, then shrugged and walked back to the counter. “None of my business,” she said, “but I’d appreciate it if your ‘stepson’ uses the back dressing room. I don’t want the shop to get a reputation of catering to drag queens. I’m sure you understand.”
“Of course we understand,” said Phyllis. “Now, here’s his wig size-could we see this one . . and this one . . . oh, and that one in the window I mentioned.” The saleslady retrieved wigs in my size in the styles Phyllis had indicated and took them to the back dressing room. I followed shamefaced.
Once there I tried on the wigs for Phyllis to look at, and after having me try each of them on a second time she finally decided to take the one she had first seen in the window, a long wavy blonde “showgirl” style wig. She took it to the counter and paid for it while I stood back trying to be invisible. The saleslady shot me a disdainful look as she rang up the purchase, then went back to what she was doing, ignoring us as we left.
Once again I had to carry the purchase-in its prominently marked bag-back to the car. Once there I put it in back and got in the car. Now were we done?
“It won’t be long now,” Phyllis said with a smile. “Are you getting antsy?” I glanced back at the packages in the back seat. Actually I was, but I said instead, “Are we going home now?” She noticed my glance at the back seat and laughed. “I think you are anticipating our little dress-up session,” she said. “But no, we have a couple of more stops to make.”
The next stop was one she did on her own, leaving me in the car. It was in a rather seedy part of town, where I knew there were a number of adult bookstores, and I couldn’t imagine what she had in the packages she returned with. Next we drove to a neighborhood known for its many antique stores, and again I was left in the car while Phyllis shopped-this time for a considerable while. She returned with a largish bag full of boxes, which she put with the ever-growing pile in the back seat. “Now our last stop,”she said. “They’re expecting us.”
I couldn’t imagine what she meant, but it became clear as he pulled up in front of our destination: a beauty parlor. I stared at it aghast and looked at her. “You don’t mean-” I began, but she cut me off. “What did I say about questioning me?” she said. “You will do as you’re told. Get out of the car.”
I did so and followed her in to the salon. She stepped briskly up the counter, her high heels clicking on the tile, and said, “We have a two o’clock appointment for a makeover.” The girl at the counter looked at her book. “Oh, yes,” she said. “With Clarice. Right back there.” Phyllis led me to the back of the salon where the girl had pointed. “Clarice?” she asked. The woman at the chair smiled and said, “Yes-you must be Phyllis?” Phyllis smiled and took her wallet out of her purse. “That’s right. Now, here are the instructions I said I’d bring.” Phyllis handed Clarice a list and a wad of money, which the beautician took and slipped into her pocket. She looked at the list for a long moment. “This is pretty-elaborate,” she said, “but not unheard of, I guess. Generally we get this sort of request a!!t Halloween, or near Mardi Gras. Is it for some sort of costume party?”
Phyllis looked at me, then at Clarice. “Not really. He just wants to look like a woman for awhile. Isn’t that right, dear?” She looked back at me expectantly, and I had no choice but to agree. “Yes,” I said, my voice cracking. “That’s right.”
Clarice looked at me with surprise. “Well, whatever. It takes all kinds. But like I said, this is an elaborate process. Are you sure you want all of this done?” She was looking at the note, the contents of which were unknown to me. I could see Phyllis out of the corner of my eye giving me a look. “Yes, I’m sure,” I said. Clarice shrugged. “Let’s get started, then,” she said.
Clarice started to seat me at the chair in back, but Phyllis stopped her midway and insisted we use the front station of the shop, clearly visible to any passersby. I was seated there, facing the window, and given a pink smock to put on.
“His facial hair is faint, so this part won’t take long,” Clarice said thoughtfully. She proceeded to give me a thorough, and occasionally painful, facial waxing, then moved without pause to my eyebrows. “Just a little shaping,” she said, taking out a pair of tweezers. I gulped and sat very still as she pulled hair after hair out, not daring to speak.
But it was especially hard to stay quiet when she took out a wicked looking pair of eyelash curlers. She used the device on my eyelashes, commenting on their natural length and fullness as she did so.
Finally she took out a jar of liquid foundation and began to dab it judiciously on my face. Then she busied herself with lighteners and darkeners and blush and such. It seemed to take forever. The warm salon was making me sleepy, and I kept drifting in and out of daydreams. Occasionally I was aware of someone walking by on the sidewalk doing a double take, but I was nearly beyond embarrassment by then.
The next thing I knew Clarice was discussing something with Phyllis, then my stepmother went out to the car and returned with the dress bag and wig box. Clarice studied the color of the gown and wig, then spent some time picking out eyeshadow and eyeliner colors, which she then began to apply. This also seemed to take forever, but finally she finished. Next she took out a black eyebrow pencil and used it on my newly-trimmed eyebrows, and then she twisted open a tube of glistening black mascara and carefully applied it to my curled lashes.
Clarice took out the dress again and used it to check next to lipstick shades. She chose a pot of lipgloss and used a lipbrush to meticulously outline my lips. She then twisted open a fullsize red creme lipstick and took my chin in her other hand, but Phyllis stopped her. “Let me do that,” she said. Clarice shrugged and handed her the lipstick as Phyllis cradled my head in her left hand then gave me a thorough and tender lipsticking.
“Let’s take care of those tacky fingernails next, shall we?” Clarice said brightly. She was obviously getting into the spirit of the affair. She led me to the nail station and went through the rather involved process of fitting me with acrylic nails. Eventually I had a set of long, curved faux nails with two coats of glossy lipstick red nailpolish.
“I think that should do it,” Phyllis said, getting up to settle the bill with Clarice. “I’ll take care of the wig at home.” I stood up to follow, but when I turned I was face to face with a mirror, and caught the first glimpse of myself since being seated.
My heavily made-up eyes widened in disbelief at the change in appearance. I had the face and nails of a beautiful twenty-year-old woman-but the haircut and clothing of a teenage boy.
Amid some laughter and a couple of derisive comments I walked back to the car, again carrying my dress bag and wig box. Phyllis strolled to the car and took her time opening it, giving a number of people a good look at my bizarre appearance. Finally we were seated in the car. Phyllis beamed at me. “All right, my little sissy,” she said. “Let’s go home and give you a good dressing.”
Part III
My stepmother slathered shaving cream all the way up my slim leg, then slowly and fussily began to shave it. I could only watch in growing horror-now everyone would know!-but she was maddeningly unconcerned. She continued to shave my other leg, then my stomach and chest, and even my underarms. It was pointless to resist.
I was oiled, powdered, and perfumed, then led back to the bedroom. As instructed, I was wearing nothing but a tight gaff-like garment, which held my penis and testicles tucked back between my legs. When we got to the bedroom Phyllis began to open boxes.
The first box was from a “sex toys” shop, and the first item she took out was a pair of startlingly realistic rubber breasts. I watched, fascinated, as she glued them to my hairless chest then used a touch of body makeup to touch up the feathered edges. They looked absolutely real.
Next I was dressed in a special padded panty-girdle, which gave me hips and a bum, and then she took out my new lingerie. She showed me how to put on the front-closing red satin-stripe bra and matching garter belt, then had me sit on the bed so she could roll a pair of silky red stockings over my smooth legs, and hook them to the garter belt. It was an incredible sensation-I thought I might swoon.
Finally she had me stand so she could lift the full red satin slip over my head. As the heavy folds of satin rippled down my feminized body chills raced up and down my spine.
“Sit at the vanity now, dear,” said Phyllis. Her voice was getting slightly husky. I sat, and watched with growing anticipation as she tugged a tight nylon wig cap over my short red hair. Then she took the glorious wig off its stand and stretched it over my head. As the silky blonde tresses tumbled onto my bare shoulders I shuddered deliciously, then looked in the mirror at a vision from my dreams.
The wig was a tousled vanilla blonde shoulder-length showgirl style which framed my salon-perfect face and spilled down over my shoulders. The slip amply displayed my “cleavage,” and as I stared at the lovely woman I had become I felt disoriented, almost like I was having an out-of-body experience.
“Please pay attention,” Phyllis said in an exasperated voice. I looked up, startled, to see her holding the gown I had chosen. I got up and walked to her as she held it up by its shoulders, then stepped into the skirt. Phyllis helped guide my long-nailed fingers into the fluttery cap sleeves, then showed me how to shrug into the shoulders one by one. Finally she reached down and zipped up the long back zipper, and the satin gown molded itself to my feminized body, and once again I felt faint.
The gown had a 3/4-length hobbleskirt, princess bodice and plunging V-neckline. Phyllis knelt and slipped her own red patent leather pumps onto my feet, and as I rose up on tiptoe-they had four-inch heels, like most of Phyllis’ shoes-I could feel the gown hang better, and I could feel myself feeling more and more like a woman. As I stepped carefully forward in the unfamiliar heels the satin gown rustled deliciously against my silk-clad legs.
I turned to see Phyllis watching me with a pleased, even triumphant, expression. “Yes,” she said, “I think ‘sissy’ is a very good word indeed. Or perhaps ‘princess.’ Shall we dress you in your jewels now, your highness?” She had opened yet another bag. “I had such fun shopping at the antique stores,” she said. “Let’s see . . . let’s start with this. Put these on first, please.” She handed me a pair of white satin above-elbow fingerless gloves as she took an antique rhinestone cuff bracelet out of a box.After I had slid on the gloves she took my left hand and draped the heavy piece over my frail, satin-clad wrist. She clasped it in place, then took my right hand and slipped a large ruby-and-rhinestone cocktail ring over my fourth finger. It was made of a large oval ruby, and rimmed with a double row of rhinestones. It looked huge on my dainty hand. !s1 The earrings matched the ring, and when the oversized oval clipons were in place I could feel them tugging slightly downward on my lobes.
“Now,” said Phyllis, “I think you will especially enjoy this.” She took the final piece of the ensemble out of its box and held it up for me to see. The V-shaped necklace consisted of numerous round rubies set in an intricate web of rhinestones. I gasped aloud. “I’d like you to ask for this,” said Phyllis softly. “Ask me to put it on you.”
I hesitated, but wanted to wear the regal necklace more than anything I had ever seen. “Yes,” I said. “Please, please put the necklace on me . . .” Phyllis immediately stepped behind me and sensously draped the necklace around my neck, then closed the double clasps and allowed the full weight of the necklace to settle into place. It rode up my neck, hiding my Adam’s apple, and the bottom of the V in front nearly dipped into my cleavage. I felt like a queen.
“This won’t fit you exactly, but it will do,” Phyllis said, taking a cleaner’s bag out of her closet. She opened it to reveal her full white sable cape, which she laid over my shoulders, and just as I was reacting to the way it felt she had taken out one last box from the antique store. “One more thing for my ‘fairy’ princess,” she said, settling the elaborate rhinestone-and-crystal tiara into place. Then she stepped back and watched, bemused, as I stood and stared at my reflection.
“Walk across the room,” said Phyllis. “Then turn and walk back this way, and spin for me-pretend you’re a model.”
I did as she said and minced carefully across the room and back, then slowly turned around completely for my stepmother’s approval. She stood up and had me turn away from her again, so she could carefully readjust the large red satin bow at the bottom of the dress’s back.
“Now come with me,” Phyllis said. “I want to get some good photos of you.” She helped me walk down the stairs, then led me out to the back yard. She posed me in front of the rose bushes and took a number of Polaroids of me, as I nervously scanned for neighbors. Then she took me back inside and had me sit on the velvet settee in the parlor, where she took a number of portrait photos.
Finally she took me back upstairs. To my disappointment, she began to strip me of my lovely jewelry ensemble, which she laid out carefully on the dressing table. Then she had me turn so she could unzip my gown. Dressed in just lingerie and heels, I was then directed to her large canopy bed, where I was to pose some more. I sprawled on the satin comforter seductively as Phyllis took shot after shot until she had used the last of the roll.
She changed film, then set the camera’s timer on and began to take a series of sequential shots. It clicked and whirred as it recorded her redressing me in the gown, then she moved it closer to the vanity where she set it to take pictures of her putting the earrings, bracelet, ring, necklace and tiara back on me.
I stood again and we did a photo shoot of her draping her ermine over my shoulders, and then she finally ran out of film.
“I’m going downtown now,” said Phyllis abruptly. “Can you amuse yourself till I return?” I blushed prettily, and she laughed. “Yes, I’m sure you can,” she said.
When she had gone I preened and strutted in front of the mirror for hours, running my long-nailed hands over my exquisitely feminized body. I was completely swept up into the fantasy outfit by then. I began to think of the image in the mirror as a real woman, and as I continued to admire my reflection I noticed that I was beginning to act, and move, more like a woman. It felt like an out-of-body experience, like it had when Phyllis put my wig on me, but this time it was ten times more so. I had become the woman in the mirror.
In fact, I don’t think it even surprised me when I turned and found a prince by my side. He had blond hair and an angelic face, and was dressed in an elaborate period outfit. I looked down at his soft leather slippers, and white silk stockings, then slowly took in his satin-trimmed velvet pantaloons and tunic. He had a white silk shirt on underneath, with billowy sleeves and high, ruffled collar, and wore a velvet cap, and was heavily bejeweled in a princely manner. I looked into his eyes, melted into his arms and we kissed like lovers.
I was vaguely aware of someone removing my bracelet and dinner ring, then I caught sight of Phyllis out of the corner of my eye, as I felt her unzipping my gown. As I let my arms hand limply Phyllis pulled the dress down off me without the two of us pausing in our kiss. Then I felt myself being guided to the bed, and then I was on my back clad only in bra, panty, garter belt, stockings and heels. I still wore my regal necklace, earrings, and tiara as well.
My “prince” took off his clothing then, and I saw with considerable surprise that he was wearing a black silk satin teddy underneath. My eyes widened more as I noted his smoothly shaved legs, chest and stomach. He smiled sweetly at me, then walked over and sat at Phyllis’ vanity.
He began to quickly-and very competently-give himself a makeover, as Phyllis walked into the room with a trunk-style suitcase. As I watched, still amazed, she opened it and took out a sleek, long black pageboy wig. She brushed it out a bit, then put it on a wigstand and continued to unpack.
When I finally glanced at my prince again, I did a double take. He was now almost a she. As he/she put on the wig liner, and Phyllis carefully settled the gorgeous wig in place, the illusion was complete.
As I watched, mesmerized, Phyllis undressed her ingenue, then glued in place the same type of rubber breastforms as I wore. It didn’t have quite the same effect, however, as “she” also sported a raging erection.
Carefully avoiding contact with any private parts, Phyllis redressed her in a black satin bra and garter belt, black silk stockings, a short black satin slip, and black patent leather high-heeled pumps.
My she-prince then walked over to the bed and paused. “I want jewels, too,” she said, with a slight pout. Phyllis said, “Oh, of course you do, princess. Here, I’ll pick something out of your jewelry box for you. Put these on first, Elizabeth,” she said, handing the pretty brunette a pair of long black satin gloves.
“Yes, mistress,” said Elizabeth, sliding on the elegant above-elbow gloves. Phyllis beamed at her and handed her oversized rectangular rhinestone clipons, which Elizabeth fussily put on. Meanwhile Phyllis had taken out a wide solid rhinestone collar necklace, and as Elizabeth finished adjusting the earrings and sat back in the vanity seat Phyllis stepped behind her and draped the necklace around Elizabeth’s slim throat, clasping it in place.
Elizabeth finally rose and looked at me again, then knelt on the bed and started to climb on top of me. However, she stopped abruptly again and went back to the vanity. “I want to wear her bracelet,” she said to Phyllis, in a spoiled voice, “and her ring.”Phyllis placated her. “Of course, dear,” she said, retrieving the antique rhinestone cuff bracelet from the dressing table. She laid it over Elizabeth’s outstretched limp left wrist and clasped it in place, and as it slipped down slightly against her dainty hand she and I locked eyes, and she smirked a little.
She casually picked up my dinner ring and slipped it over her satin-covered right ring finger. It fit a bit loosely, since she is even more petite than I am, and her hands more delicate, and her features even more effeminate. I stared at her, my breath becoming rather ragged. I very badly wanted her on top of me, soon.
She suddenly stood from the vanity and in two strides was at the bed and sliding on top me, so quickly it took my breath away. We kissed hungrily as we dry-humped, our satin lingerie sliding together deliciously. She ran her satin-clad hands all over my body, knowing just where to touch me, paying special attention to my faux breasts, my richly bejeweled throat, and my silky legs.
The Polaroid camera was again clicking and whirring, but I paid it no mind as I used my inch-and-a-half inch nails to softly rake across my lover’s satin covered back and bum. “I want you inside me,” I thought, then suddenly realized I had actually whispered it.
“I know,” Elizabeth whispered back. She reached under my slip and undid a velcro closure on my panty-girdle, and I suddenly felt a satin covered hand brush against my anus. At the same time she had undone my gaff, so my half-erect penis popped out, and I came prematurely. Elizabeth eyed me curiously. “Oh, my,” she said. “Your stepmother didn’t tell me you were a virgin. We’ll start a little slower.”
She got up, stripped herself of ring and glove, then picked up a jar of lubricant. She lifted my slip and thoroughly lubricated all around and in my anus, her delicate fingers tickling my bum in a delightful way.
Then she again slid on top of me, taking me in a long, soulful French kiss as she slowly began to fuck me.
She barely entered me at first, just with the tip of her glistening erection, then began to tentatively hump me. Little by little she penetrated further, and at some point I realized with surprise that she was slowly buttfucking me all the way to the hilt.
She kept up the languid pace while we kissed and fondled like teenagers on a prom date. It might have been a half hour later that she finally picked up the pace, and began to hump with with abandon. I lifted my high-heeled feet to her bum, helping her to penetrate me, and I think I actually screamed in ecstasy when I felt warm, thick come spurting up inside me. I came again then too-in the longest and strongest orgasm I’ve ever had.
Part IV
We lay sprawled together, exhausted. Phyllis took yet another picture, then sat next to the bed and looked at us. “Well,” she said, “I think we have a few things to talk about.”
She turned to me first. “Bertie has been my regular hairstylist for five years,” she began. “And quite soon after I started going there I found out that Bertie liked to go out in drag occasionally. He always passes, of course.
“Well, I’ve been dying to dress a boy up since-well, since Trish dressed you up when you were little. Do you remember that?” Of course I did-it was a very fond memory-and I nodded, then frowned and said, “How did you know about that?” Trish is my older sister, but the dress-up sessions ended when I was only eight or nine, years before Father remarried.
“Oh,” Phyllis said brightly, “Trish told me-did you know she even has photos of you as a little ‘girl,’ and shows them to people?” I blushed hotly-several of those outfits were, as I recalled, rather elaborate, and I had no idea Trish had kept any of those photos.
“Anyway,” Phyllis said, “I’ve been a bit fascinated with the whole idea for a while now-and when I found out that Bertie was a drag queen I got up the nerve and asked him if he would let me dress him up. Obviously, he said yes. We’ve had a ‘session’ here at least once a month for the past four years.”
My head swam as I took it all in. Phyllis had been dressing this, this drag queen in our house, all that time, while I dreamed of having the same done to me. It seemed so unfair.
But then Phyllis said, “But then one time Bertie was over here visiting-you know, just as Bertie-and your sister stopped by. She happened to have that little photo album I mentioned-”
“Oh, dear, I forgot-I still have that,” Bertie/Elizabeth said. She hopped off the bed and got a photo album out of her trunk. She handed it to me, and I opened it to find seemingly every one of my early “dress-up” sessions recorded on film. I of course remembered being photographed, but I guess I never thought about what had happened to the photos. It was simply appalling that total strangers were looking at them.
The first ones were when I was four or five, and were the usual dress-up outfits of blouse, headscarf, beads, clipons and lipstick.
As I got older, though, the dress-up sessions slowly became more elaborate. Eventually I was being dressed in blouses and skirts, with matching patent leather pumps, belt and purse. Trish began dressing me in nicer jewelry as well, and also convinced me to let her add “just a touch” of eye makeup in addition to lipstick and rouge.
Finally I turned to the next to the last page, and saw that it contained several photos of the last time Trish had dressed me. I remembered it well.
It was when she was home from college-that’s right, she did dress me once after she graduated, so I guess I must have been . . . Ten? Almost eleven?-
I glanced at Elizabeth and she smiled warmly. “When I saw that one,” she said smugly, I knew you’d still be a ‘dresser. I mean, you’re practically a teenager here.”
It was true. And the outfit! Trish had dressed me in her prom outfit-complete with the matching lingerie, which I had never worn before then, and her dainty rhinestone earrings and necklace. It was also the first time she had dressed me in a wig, and it was my first real makeover. I really did look like a teenage girl.
Finally I turned to the last page in the photo album. It was an 8×10 of one of the portrait shots Phyllis had taken of me that afternoon in the parlor. “The girls at the beauty shop just loved that one,” Elizabeth said. “As for me-well, I almost soiled my jeans when I saw it.” I stared at it, then at Phyllis. “Oh, don’t worry, we’ve just shown these pictures to a few people,” she said. “A few who . . . understand femme boys.” One of these days I’d like to take you in to meet some of them. Wouldn’t you like that?”
My mind whirled with the possibilities. “Yes,” I said, surprising even myself, “I believe I would!”
The End
