First Preparations

       Edward’s first portrait sitting was arranged for the following Tuesday after school. He was excused from his usual piano lesson, which made the portrait seem slightly more agreeable. By four o’clock, however, with the school day behind him and the whole afternoon somehow already claimed, he had begun to realize that his music lesson might have been easier.

       Soon after he got home from school, Aunt Patricia arrived with a large white box tied in pink ribbon and announced that she had brought “a little gift to begin properly.” Edward didn’t know exactly what to expect, but he hesitantly opened the large box. He lifted the cardboard lid and gasped involuntarily at what he saw. Inside, folded in tissue paper, lay a summery pink girls’ dress with a rounded collar and flouncy flutter sleeves! The adorable dress had a ribbon tie at the waist and a flared skirt. There was also a pair of pristine white tights, a delicate pair of satin panties trimmed in lace and a shiny pair of black patent Mary Janes shoes. 

       Edward stared at the clothes in shocked surprise. “Who are these for?” he asked futilely, though there was no one else in the room they could possibly fit. “You mean…?”

       Aunt Patricia interrupted with a smile. “Of course. Miss Vale and I had a long chat. Sitting for a proper portrait means getting you into the proper frame of mind. If you are truly to echo your great-great grandmother as a young girl, Miss Vale and I think that achieving that right girlish mindset is crucially important.” Her lips curled in a slight grin as she continued, “I suggested to Miss Vale that getting you a dress of your own to might be an elegant way to accomplish that. She giggled a bit, but then she agreed that it would probably do the trick.”

       Edward looked disbelievingly at his mother as he tried to process what was expected of him now. Aunt Patricia had gone too far! Unfortunately, he was deflated when he saw his mother’s reaction. His mother gave him an almost apologetic look as she gently lifted the dress from the box. “Miss Vale says proper preparation for a true portrait begins well before you are in front of the artist, dear,” she began softly.

       Aunt Patricia piped in, “your mother is right, sweetie, and you’ll need to get into a more feminine frame of mind to do your great-great grandmother justice.” Then she beamed and practically licked her lips, “You’re going to make an adorable little girl!”

       Edward opened his mouth in protest, but no words escaped. Over the past couple of days, he had tried to come to grips with the idea of posing for a portrait dressed as a girl. He hadn’t dared mention it to anyone at school, and he was already worried that somehow they would find out. As he had wrapped his brain around the prospect, he had at least taken solace in the fact that it would just be something he did in the privacy of the artist’s studio.
 
       Now, his Aunt Patricia had breezily tossed aside those expectations. With a sinking feeling, he realized he would be wearing this monstrosity of a dress when he left his house today. His cheeks flushed red. What if someone saw him? He grimaced as he realized that preparing for his portrait sitting would be its own process.

       Then, things begin to happen fast. In short order, Edward was swept helplessly along as his aunt and mother set to work on him. He was ushered into his mother’s large bathroom to get ready. Soon, he was getting scrubbed clean as if he were going to church. His mother pulled off his tee shirt and went to work on him with a damp washcloth and some sweet-smelling soap. Then, his face, hands and ears were washed, and his fingernails were brushed free of dirt.
 
       Once he was deemed suitably clean, his mother held out the lacy pink satin panties from the box and said, “Put on your panties, dear, while your aunt and I wait for you in the bedroom.”
 
       In a tiny voice, Edward asked, “can’t I at least wear my normal underwear?”  He added helplessly as he grasped at straws, “no one will know…”

       â€śYOU will know, sugar,” Aunt Patricia chimed in with a chuckle, “How could you possibly feel girlish wearing your boring boys’ briefs?”   

       Wordlessly, he took the lacy garment with a look of disbelief. He stood almost frozen holding “his” panties as his mother and aunt walked into the bedroom and closed the door behind them. Alone in the bathroom, he stood there several seconds just looking at the satiny underwear he held gingerly between his thumb and index finger.

       â€śDon’t dawdle now, Edward!” his aunt called loudly from outside the door, “we don’t have time to waste!”

       â€śYes… Aunty,” he replied meekly. Cringing, he slipped off the khaki shorts he had been wearing. Then, with a feeling of helplessness, he pulled on the panties. He shivered as the silky, lace-trimmed fabric slid over his skin. He saw there was a precious little pink bow on the waistband in front as he pulled them into place. After several more moments, he reluctantly emerged red-faced from the bathroom, holding his hands uselessly in front of him.
 
       â€śOh my goodness, how darling!” Aunt Patricia exclaimed when she saw her pantied nephew for the first time.

       Edward just stood there speechless while his mother smiled nervously.  Everything seemed to happen in a blur as he was quickly cocooned into the precious new outfit his aunt had bought for him. His mother helped him pull on the clingy white tights, and his pulse quickened as they slid up his slender legs. Next, it was time for the dress… his dress. His aunt held it out and gestured for him to step into it. She pulled the darling sleeves over his arms and then cheerfully buttoned him into it. As he felt its delicate contrast mesh top wrap snugly around his chest, Edward was dismayed how well everything seemed to fit. The generously ruffled short sleeves settled cutely over his shoulders, the ribbon circled his waist daintily, and the bouncy skirt fell to precisely the right length just at his knees. His mother buckled the perfectly sized Mary Janes neatly onto his feet while Edward stood helplessly at the rapid turn of events.

       Aunt Patricia watched with open approval. “There,” she said. “I see I got the sizes just right. Just look how naturally his dress drapes him, Marian.”

       His mother nodded quietly. Edward got his next unpleasant surprise when she sat him down at her vanity and reached for a bottle of nail polish.

       â€śNail polish, too?” he managed to squeak.

       â€śIt was your aunt’s suggestion, sweetheart,” she explained a bit sheepishly.
As she brushed pale pink polish onto the first nail, Aunt Patricia explained, “It will make your nails look much neater, and it will complement the rest of your adorable outfit, dear.”
 
       â€śIt’s just a hint of color, dear,” his mother added almost apologetically. He watched in glum disbelief as she painted all his fingernails with the pale pink polish.

       Edward held his fingers apart while the polish dried to a glossy shine. He felt so sissyish and absurdly aware of his own hands. While his nails dried, he watched in the mirror as his mother tied his golden-brown hair back in a loose ponytail with a pink satin hair ribbon “to keep things tidy.”

A Rainy Saturday

       In the late spring, when school afternoons began to feel brighter, and summer was just around the corner, thirteen-year-old Edward Gray sat down awkwardly in the family den to play a video game. It was a rainy Saturday afternoon, the sort of afternoon when the windows blurred silver and the cozy house smelled faintly of potpourri. As he logged in, he absentmindedly wondered what his mother and Aunt Patricia were up to in the dining room.
 
       He sighed slightly as he rejoined his game. He quickly realized that he couldn’t really concentrate on his game with his aunt here, especially with the way he was dressed at the moment. He had always felt a little self-conscious around his Aunt Patricia. She had been a constant figure in his life in particular after his father passed away several years ago. She was very well-off from a long-ago divorce settlement, and he vaguely knew she helped his mother out financially. He didn’t know much about the specifics. She had always been kind and generous to him and his mother, but often it all felt… smothering. With a subconscious shrug, he tried to shift his attention to the game.
 
       Meanwhile, his mother and Aunt Patricia were going through some old family items in the dining room. Earlier, they had opened a long cedar chest that had sat untouched in the corner of the dining room for years. They now had a small collection of family odds and ends spread out on the large dining room table and were sorting through them.
 
       â€śI told you Marian!” Patricia exclaimed, “look at that old photo… the resemblance is uncanny!”

       Marian Gray looked at the old, sepia-toned photograph in her hand with a new appreciation. She hadn’t seen this photo in years. The oval photograph in a tarnished silver frame depicted a demure young girl who sat very straight up in a pale Victorian gown on a carved wooden chair. Her eyes were lifted as if she had just heard someone call from another room. “It is striking, Patricia,” she had to admit. She looked from the photograph in her hand to the partially unwrapped package on the table before her. The old tissue paper crinkled at the touch, and it smelled of lavender sachets and the deep, secret scent of old cloth.

       â€śLet’s just see what he thinks,” Patricia urged. After a brief pause, Marian nodded silently.

       In the very next instant, Edward heard his Aunt Patricia calling him. “Edward, dear,” Aunt Patricia’s voice rang out, “would you come join your mother and me in the dining room, please?” Although it was phrased as a question, her tone was insistent.

       Edward was annoyed at the interruption. He grimaced slightly. Although he had learned over time it was usually best to see what his aunt wanted, he was tempted to just keep playing. After another few seconds, however, he thought better of it. He reluctantly paused the game. It was nearly impossible to ignore her, and stalling usually just made it more uncomfortable.

       As he stood up from the couch, he heard her voice again, this time louder, “Oh Edward sweetie, did you hear me? Your mother and I are waiting for you!”

       â€śI’m coming… Aunt Patricia!” he called back. She always looked a little peeved if he didn’t address her as “Aunt Patricia” or “Aunty Patricia” or sometimes just “Aunty.” He always tried to remember to add that and forestall any additional drama. It all kind of seemed silly to him, but he had no interest in rocking the boat when it came to his aunt.

       Rounding the corner into the dining room, Edward saw his mother and aunt standing next to the open chest. His mother was holding what looked like an old dress that Edward had never seen. His Aunt Patricia hovered beside her sister with an eagerness she did not bother to conceal. The dress, Edward would soon learn, had belonged to his great-great grandmother. As Edward looked at it curiously, it seemed to him less like clothing than a preserved piece of another century.

       â€śMy goodness it took you so long I thought we might have to send out a search party!” his aunt chided him with a cheerful smile.

       Although it had been no more than twenty seconds since she first called him, Edward replied meekly, “Sorry… Aunty.”

       â€śOh you little rascal,” she said with a barely stifled giggle, “always up to some shenanigans!” Then, for the umpteenth time it seemed, she beamed, “I still can’t get over how handsome you look in that darling suit!”

       Edward cringed to be reminded of his attire, but he kept silent. If anything, he was a meek and obedient child most of the time compared to his peers. He was naturally shy, and now in his adolescence he tried to avoid the spotlight even more. For a moment, his thoughts drifted.

       He was well aware of certain things about his appearance, mostly because other people often mentioned them. For example, his mother had always kept his light brown hair a little long for a boy. It was not deliberately fashionable but difficult to keep trimmed because it curled at the ends and never seemed to lie as short as he wished. His face, too, had a delicacy he could not deny: a narrow chin, fine-boned cheeks, dark watchful eyes, and a mouth that looked more thoughtful than bold. He did not dislike these things exactly, but he knew by now that they projected a certain softness to others.
 
       His Aunt Patricia had always noticed these things too. She had no children of her own, and so, from the time Edward was small, she had poured a great deal of her unused attention onto him. She was loving in her way, lavish and admiring, but her admiration often made him uncomfortable because it seemed to pass over everything boyish about him and settle instead on what she called his prettiness. “Such a pretty child,” she would say, smoothing his hair or turning his chin toward the light. “Those eyes, Marian. And that mouth. Quite refined.”

       Over time, Edward had learned to endure the remarks by pretending not to hear them. Her gifts to him had always followed the same pattern. Other boys received baseball gloves, toy race cars, model trains or video games. Aunt Patricia brought Edward things like fine stationery and monogrammed handkerchiefs. She once presented him a porcelain keepsake box for small photos and trinkets, and another time he received a little velvet case containing pearl shirt studs for occasions Edward could not even imagine. She seemed to have no conception of what a typical boy might want. Everything she chose was polished, scented, folded in tissue, or tied with ribbon, as if refinement itself were a present. It seemed to Edward that she meant every gift kindly, but her generosity always leaned in a very particular direction.

       For his birthday when Edward was ten, for instance, Aunt Patricia had arrived with a parcel about the size of a book, wrapped in ivory paper and tied with a satin ribbon so pale it was nearly white. Edward had accepted it with a slight sense of trepidation.

       â€śOpen it carefully,” Aunt Patricia had said, settling beside Edward as if the ribbon itself deserved respect. Inside was a small leather case lined with blue silk. Nestled in it lay a silver-backed hand mirror and a matching comb, both engraved with a delicate spray of lilies.

       Edward stared, unsure what expression would be safest. “For me… Aunt Patricia?” he had asked with a squeaky little voice.

       â€śOf course, sugar,” Aunt Patricia had gushed, delighted. “For that lovely honey brown hair of yours! A young person with such refined features ought to have refined things.”

       The mirror was beautiful; that was the trouble. It was cool and heavy in his hand, made with a care he could not dismiss, and yet it seemed meant for someone quieter, prettier, and more willing to be admired.

       â€śThank you, Aunty,” he had croaked, because Aunt Patricia had been watching him with such hopeful pleasure. She had kissed his forehead and smoothed the hair the comb was meant to tame.

       â€śThere,” she said cheerily. “I knew you would appreciate it.” Edward did not know whether appreciation was the name for what he felt, but he kept the case closed in his drawer for months, taking it out only when no one could see.

       And just last year, when he was twelve, she had announced her intention to buy him a proper new suit for Easter. This had all sounded innocent enough until he saw it on Easter Sunday morning. When his mother brought a pink garment bag into his bedroom and unzipped it, Edward recoiled and cringed at how childish and fancy it was! With a looming sense of dread, he had pleaded with his mother not to make him wear it, but she insisted. Aunt Patricia was coming over soon, and they were all going to a fancy Easter dinner at his aunt’s country club. His mother had told him almost sympathetically, “Sweetheart we can’t disappoint your aunt after she made all this effort for you.”

       When Aunt Patricia had swooped in to pick them up, she had gushed over how handsome and refined her nephew looked dressed in the monstrosity.  “Absolutely gorgeous,” she had proclaimed. “It fits you beautifully, sweetie! It makes you look so cultured and dapper!”

       Edward’s exquisitely tailored “proper new suit” was a baby blue wool blend, and the coat was actually a little waistcoat paired with matching blue knee pants that gathered with elastic at the knees! Underneath the coat, he had been buttoned into a billowy white silk shirt with French cuffs and subtle ruffles down the front. A baby blue ribbon tie was daintily knotted at the rounded collar, and the floppy silk bow looked much more prissy than handsome in Edward’s opinion. Crisp white knee socks and a pair of matching baby blue loafers had completed the juvenile look. He had felt like such a sissy!

       â€śThank you, Aunt Patricia,” he had managed to spit out. After a reproving glance from his mother he had reluctantly added, “It’s very nice.”

       Then, as if that weren’t enough, she had presented him with another daintily wrapped Easter gift. The wrapping paper was patterned with vintage Easter bunnies and tied with a fancy pink bow. When he had tentatively opened the second box, he discovered a large vintage doll. The doll was a young boy with lifelike features and honey-brown hair dressed in a darling blue suit that exactly matched the one he had been wearing!

       His aunt had beamed as he held it up gingerly, “Now you have a little twin! Isn’t he precious?”

       Flabbergasted, Edward had been at a loss for words.

       His mother had piped in, clearly taken aback but trying to be polite, “It’s... quite charming, Patricia!” then with a pointed look at her son, she added, “and what do we say Edward?”

       â€śTh.. thank you... Aunty,” Edward had stammered, “It’s… great.”

       The elaborate doll now sat prominently displayed on a shelf in the den. He shuddered as he recalled the memory of all the people at the country club gawking at him and the muffled giggles he occasionally heard from other children at nearby tables. No one else had been dressed in anything remotely like the outfit he had worn. He had felt so sissified wearing it, especially with the way his aunt had continually adjusted his floppy bow and brushed invisible lint off his coat throughout the dinner. Ever since, his pretty doll on the shelf had been a constant reminder of the experience, and the horrible suit still hung menacingly in his closet.

       To his chagrin, Edward was fastidiously dressed in that same fancified and juvenile suit today for his aunt's visit.

Chapter 382.

The ladies snuggled back into the chairs.  Connie took a sip of wine.  They regarded him smugly.  He knew that they had him utterly at their mercy.  His erection had settled into a state of aching, expectant hardness.  He attempted, not very successfully, to conceal his arousal, keeping his hands in front of him, his balls concealed by his fingers and  the tumescent shaft behind his hand.  Even so, the gentle vibrations of the plug, which he could feel in his coc-k, made the temptation to play with it almost irresistible.  He discovered he could palpate it by the slightest flexing of his wrist, producing subtle ripples of pleasure, and coaxing little flows of juice from the tip.  Even as he was doing this, he looked at his audience with as innocent a face as he could command.
Connie put down her wine and smiled.
“Let me explain, Tim.  Cressida has asked us to make some friendly enquiries into your sexual status.  I understand you were briefly interviewed by the staff at ESDS, but she thinks we could offer a more sympathetic approach.  It is important for your employers to understand your needs, so that they’ll be able to provide appropriate support.  Now, first of all, may I ask, would you consider yourself  heterosexual?”
“Oh…  Yes, miss…”
“You do seem to be, I must say…  But there was some mention of your relationship with your fellow boot boy…   Bobby?”
“W-was there…?”
“You know there was.  I believe there was an admission of some…mutual masturbation?  Isn’t that correct?”
“W-was there…?”  He didn’t like the way the questioning was going.  He felt distinctly nervous.  He unconsciously expressed his embarrassment by awkwardly crossing his legs.
“Careful, Tim.  Don’t trip.”
“Miss…?  I c-can’t remember exactly what I said…  They were pressuring me, see?  Bobby and I, we’ve, like, always been good friends…”
“Very good friends…”
“Yes…  He’s a nice guy.  We’ve known each other since we were kids.  In fact I miss him quite a lot, now I’m with ESDS and he’s still at Pitt’s Wood.  We used to have fun…”
“Tim, please answer the question.  If you don’t, it’ll be the same as a lie, and I’ll have to turn this thing up to number three.  Is that what you want?”
“N-no, miss…  Well, I mean, maybe we did once…”  Seeing her frown, he added, “I mean, a few times…”
“Interesting.  But you’re not gay, right?”
“No!”
“This Bobby guy sounds interesting.  I think we should get you two back together.  What do you think, girls?”
“Absolutely!”
“Can’t wait!”
“In the meantime, I think you’d better explain just what you two have been getting up to, and how it all started…”

Chapter 380.

“Be a good boy, Tim,” added Frieda, “Do what your told, and tomorrow…we might give you a very special present.  Right, Connie?”
“Well, yes…  But he would have to be very, very good…”  She gave Tim a mischievous smile.  “It’s something any boy of your age would be delighted to have, Tim.  Hardly any actually possess one.  It’ll be yours to keep.  However, whether or not we decide to give it to you is dependent on your being polite and obedient today.   Do you think you’re up to it?”
Tim was curious, but suspicious.  In any case, he had realised he had no choice.  There was always an underlying threat of punishment.  He wasn’t afraid of the whip, but if they decided to release a picture or a video...or even showed him off in public…  His cheeks burned at the thought.  Above all, he must keep his work for ESDS completely secret, and quite separate from his outside life.  So he made a decision; to be totally compliant and obsequious from now on.  He assumed a cheerful demeanour.
“Yes, miss Connie.  I think I am.  I’ll be good from now on.  I won’t complain or sulk, I promise.  So please don’t get your whip out again…”
He wanted to make her think he was terrified of the whip, so that this would seem her best deterrent.
“Good boy!  I think you really mean it this time.”
He laid it on thick. “Yes, miss.  I really do.  I understand it’s all part of my training, and I should be thankful.”
“Excellent.  Well, we have a few other outfits for you to try on.  I’ll need to release you to change, and you will return to your maid-tidy without demur.  Right?”
“Yes, miss.  Of course, miss.”
“So while you’re in girl mode, let’s see what you look like in a maid’s uniform.  Cressida especially asked for some pictures.  Cynthia’s come up with a cute one and a more formal one, both in cotton and pink latex.  I’m sure you’ll like them.  You can wear one later this week, actually, and we’ll put you through your paces.”
“Can I take him?” asked Bridget.
“Help yourself…”

Bridget helped him change.  The uniform wasn’t too bad.  The panties, though…  Pale pink latex, so fine it was translucent…  He had to turn his back to Bridget to put them on.
“This is so pretty…  Do you like it?”
“Yes, miss Bridget…  And it fits perfectly.”
“Come on then.  Let’s show the others.”

As he skipped into the room there was a chorus of approval.  For a moment, in the sudden warmth of adulation, he forgot himself, and did a little twirl.
“Gorgeous!” simpered Connie.  “Now let’s get you back on your disc.”  She led him over and chained his ankles again.
“Why do I have to be chained up, miss?”
“We need to keep you in one place for the photos.  Besides, Cressida particularly asked for it.  I gather they’ll be going on the website brochure, and she wants to make sure her clients fully understand the subjugated status of her boys.”
“Oh…”
“And of course we don’t mind, do we, ladies?”  Shaking of heads.  “Personally I love all sorts of restraints.  Especially on big strapping boys like you, Tim.  It gives me a little thrill to know you’re completely in my power.  What, are you shocked?”  She emitted a short and not very pleasant laugh.  “Later on I’m taking a few snaps of you for my own collection, and the best one’s going in a frame by the side of my bed.  Does the thought embarrass you?  Oh, it does!  Look girls, he’s blushing again!”
Tim bit his lip.  If this was the sort of humiliation he had to endure, well, so be it.  He smiled and pretended he didn’t mind.
“Show us your panties, Tim,” called Frieda, rudely.
He smiled, treating the remark as a joke, which he hoped it was.  It wasn’t.
“Go on,” said Connie, impatiently. 
He turned bright red.  This was too much.  He tried to smile, but he just looked as if he was about to burst into tears.  Reluctantly he lifted his tiny skirt.  Apart from the fact his pride and joy was squashed flat against his stomach by the tight see-through latex, he might as well not have been wearing panties at all.  He could feel them leering at him.  Connie was seized with a fit of the giggles.  For a moment he frowned and glared at her – then, remembering himself, quickly adopted an expression of pathetic, forced acquiescence.

The ordeal finally came to an end, and he was allowed to leave them room, accompanied by Frieda, to put on the formal maid’s uniform.  This one was received with genuine admiration, enhanced by Frieda's idea of adding a fully-padded bra to his ensemble.  Connie put him back on the disc, and all three of them snapped away while Tim forced a smile.
“You can wear this tomorrow and wait on us.  Would you like that?”
“Ooh, yes please, miss…”
“I think Cressida will approve.  It will be a good uniform for the posher clients.  Yes.  One more pose…  Maybe with a tray…  And then we’ll move on to something else.”

Lol, this story was loosely based on one of my childhood experiences. In writing it, I wanted to try and put the reader into the emotional anguish of a boy about to get spanked by his intimidating, authoritarian Principal.