Down a Peg
By Lauren Bliss

It was a sunny Saturday morning in 1962, when our hero, Jimmy had finally found the end of his mother’s patience. Meredith Baker had taken her four children to her mother's house for a quiet weekend holiday. Things had been stressful since she lost her husband in a traffic accident, one year prior. She thought getting away for a little while would give the kids a chance to clear their heads, and maybe even bond again, since all they seemed capable of doing lately was bickering and fighting.

Catherine was the eldest at twenty. She had recently enrolled in beauty school with big dreams of opening her own salon one day. Sarah was seventeen, and an excellent student. She had planned for university, and was ready to prove herself just as capable in the business world as any man. She was very forward thinking for the time. Susie, the youngest at fourteen, was very much a tomboy, in that she liked to play sports and enjoyed the outdoors. Still, she had a feminine beauty and grace that had the boys at school tripping over themselves for her attention. All of the sisters were saddened by the loss of their father. As would be expected, every one of them spent several months grieving, but each was coming to terms with life as it was, in their own way

Their brother, Jimmy, had just turned 16 years old. He took the loss of his dad harder than anyone. Regularly acting out, he felt it his duty to fill his father’s shoes, despite how big they seemed. He was in a hurry to prove his manhood, but found himself falling short.

Jimmy was a slight boy, with high cheekbones, plump lips, and a small, turned up nose. It’s not like he wasn’t attractive, but his face could best be described as cute, rather than handsome. The soft countenance did nothing to assuage his fleeting masculinity, and living in a house full of women who constantly reminded him just how adorable he was didn’t help. In an attempt at cultivating the image of some kind of rebel without a cause, he had refused to get a haircut since his father passed. His brunette hair now fell down to his shoulders, but he kept it in an unkempt mess tied by a rubber band. The Beatles had only recently debuted, and it was still a few years before they normalized truly long hair on boys, and not just the shaggy mop hairstyle that was currently the bane of every parent in the western world. Unwashed as it often was, it made him look dirty. His mother constantly hounded him about his disheveled appearance, often saying, "I'm too ashamed to even take you in public."

They arrived the previous night, and their mother decided that the family would turn in early, so they could get up and help their grandmother with the chores. That way they could take her out to a nice brunch after. It was Meredith's way of saying thank you for allowing them into her home. However, around eight o'clock, Jimmy refused to get out of bed. His mother came upstairs, and started threatening to not buy him the new car he so desired. "Jimmy," his mother said, "if you don't get moving, and help with the chores, not only will you not be getting that car, but you will also be responsible for feeding yourself this morning. We're leaving for the club in one hour. Get up and put your suit on…now!."

"If you insist on ruining my life, at least have the decency to do it at a reasonable hour," grumbled Jimmy.

"Put your suit on now!" she bellowed. "The only thing left to do is take out the trash anyway. Your sisters were really a big help. They were up earlier than I asked, so they’d have ample time to get dressed, before brunch. I wouldn't want to get on their bad side if I were you, now move!"

"Alright, fine!" he yelled back.

Jimmy, forgoing a shower, began his morning by putting on his dress pants, shirt, and blazer. His shoes and socks weren’t an issue, but in a clear demonstration of his lack of maturity, he had to wait for his mother to help with the tie. He went downstairs to take the garbage out, but offered no pleasantries to his mother or grandmother, who were sitting at the breakfast table.

"I’m sorry he's being so rude.” said Meredith.

"It's okay. Losing his father was hard. It’s expected for a boy his age to act out, given the circumstances.. Give him a little bit of time and he'll grow out of it." said Grandma.

Jimmy heard the end of their conversation while he finished his task, and did not take kindly to being talked about like he was a petulant child. True to character, in response, he did the least childish thing he could think of. He jumped into a mud puddle.

"Why on earth would you do that?!" Meredith shrieked.

Jimmy's response was probably as honest as he could muster. "I don't know!"

Grabbing him by the ear, Meredith led him to the mud room in the back of the house and ordered him to strip. "Everything young man! I mean it!" Jimmy disrobed, and she handed him a pink terry cloth robe her mother had loaned her. He held it like it was going to give him some kind of disease.

He yelled, "I can't wear this sissy thing!" Jimmy wasn’t trying to, but found the end of his mother’s rope. She bent him over, and slapped him right across his rear. With a newfound sense of catharsis, she kept spanking and spanking until she had nothing left and he had no resistance.

She ordered, "Now, you will go upstairs and ask Catherine to help you get cleaned up while I try to find something appropriate for you to wear. Let her make you look presentable for once, or so help me god, Jimmy."

With no fight left in him, and heavily motivated by fear, he marched upstairs, and knocked on the girls’ bedroom door. Once alerted that everyone was decent, he walked in to find Susie sitting in an armchair under a portable dryer, with her hair up in curlers, wearing her dressing gown. Sarah sat at the foot of the bed, already dressed in her white blouse, and pink knee length pencil skirt. She was wearing a smock while Catherine put the finishing touches on her make up. Her hair was short, black, and side parted; a typical pixie, much like Audrey Hepburn’s. Catherine, who was the first to wake that morning, was completely ready in her yellow floral print shift, perched atop three inch white pumps. With her makeup immaculate, and her hair teased into a small beehive with a yellow ribbon tied into a bow above the bangs, she was a model representation of mid-century femininity.

"What happened to you?" asked Sarah.

Jimmy mumbled his answer, betraying his embarrassment. "I jumped in the mud. Mom's furious. She sent me up here so Catherine can clean me up, and in her words, make me look presentable for once."

"Well, take a shower first." Catherine said, appraising her workload. "Don't forget to wash your hair, and use the conditioner, but don’t rub it into your roots."

After grumbling some inaudible response, Jimmy proceeded to the bathroom and ran the hot water. He did everything exactly as they asked him to, out of fear of their mother's retribution. Meanwhile, in the bedroom, Catherine was removing the bonnet dryer from Susie's curlers. "I don't know what his problem is." Sarah said. "He thinks he's better than us, just because he's a boy. On top of that, he doesn't even take care of himself. He’s just disgusting sometimes."

Susie chimed in, "Yeah, he used to be nicer to me, but now he just complains about how I can't play ball with him anymore, because I'm a girl. He acts like I'm good for nothing, but I’m a better ball player than he is."

Catherine added, "Also, his hair and general appearance are sub par. If I could get my hands on his hair, I'd clean it up, and show him just how many more doors would open up, if he just presented a better image."

After removing all the rollers from Susie's hair, she brushed and teased them into place, then secured a black headband in her curls. Not being old enough for makeup, Susie ran off to finish getting dressed in the other guest room. Just as she was leaving, Meredith had come upstairs, having managed to find a white button down shirt and a pair of old shorts in some of the old things left around her mother's house. Walking into the bathroom, she left the clothes on the toilet seat, and told him that his sister would fix his hair when he was dressed. "I'll just pull it back. It should be fine," he said.

"Not today, mister. Today, we're going to look as nice as possible for grandma. You hear that, girls? I want him to look nice. Don't let him leave this room, otherwise."

Jimmy came out of the bathroom, wearing the outfit his mother left. It was slightly too small, and just immature enough that he looked childish. "I can't believe she's going to make me go out in these clothes." he whined. "It's too embarrassing. I'd rather look like a girl than some kind of sissy little kid."

Both his sisters could usually tune out his tirades, but that sentence struck a nerve with both Catherine and Sarah. He didn't know it yet, but he was going to regret it. Catherine took the lead, telling him to sit on the stool while she fixed a plastic apron around his neck. "Sorry honey, but the only clean apron I have left is this." It was bright pink, with large, white polka dots.

From behind his back, she locked eyes with Sarah, and gestured to the mirror. The unspoken plan finally began to take shape, she quickly covered the mirror with a nearby towel. Sarah had been thinking earlier about how pretty Jimmy could look when she saw his scrawny legs poking out from under the pink bathrobe. It almost looked like he was wearing a dress. He had no hair to speak of below his eye brows. Apparently her sister had been having similar thoughts.

"Now, Mom told me to make you presentable, so you better not fuss or fight with anything I do. You wouldn't want to get on her bad side again, would you?" she asked as she set to trimming his hair. It seemed like she was cutting a lot, but when asked about it she said, "I'm just evening the ends." She trimmed away, with laser focus, till his hair was just barely touching his shoulders. She hoped he wouldn't notice anything weird, when she paid extra attention to the area right around his eyebrows. Next she grabbed her bobby pins and two plastic rollers, and sat them down next to Jimmy.

"What do you think you're doing?" he nearly screamed, but quickly lowered into a shrill whisper. He did not want his mom coming back up the stairs.

"I have to put it up to dry it." Catherine stated plainly, as though nothing was out of the ordinary.

"Yeah, have you ever seen a girl under a dryer without her hair up in something?" Sarah asked, knowing he had no idea. She probably could have convinced him it was normal to brush your teeth with beet juice.

"I guess you're right," Jimmy said, not wanting to appear ignorant.

Catherine coated his hair in setting lotion, and set to pin curling it all around the crown, back, and sides. She then took the two rollers, using them to wind up his new bangs, and then fitted a hair net over his head, before he could touch it. Meanwhile, Sarah went downstairs to find a nail kit she had used the night before on Susie. She arrived back upstairs just in time to find Jimmy being led to the armchair and having the dryer fit onto his head. Catherine told him, "Your eyebrows could use a little work. I'm sure it'd make Mom happy." With no idea what she was talking about, he agreed.

Sarah interrupted, "I went downstairs. Mom said to make sure your nails were clean and mud free as well." She set to work on his nails while behind his back Catherine set up her waxing equipment. Jimmy would never admit it, but it was extremely relaxing being pampered, so he easily fell asleep again.

It was nine forty-five when he stirred again. Rather than gently being coaxed awake, Jimmy was ripped from his slumber, much the same way as the hair was being ripped from his brow. The sisters had ripped off a wax strip each, just as his hair had finished drying. He was still so groggy that it did not register as anything other than a rude awakening. They guided him back to the chair half asleep where both his sisters started removing all of the bobby pins from his hair. Catherine said, "I just need to comb your hair a bit, so that it doesn't look like a tangled mess."

"Whatever," Jimmy replied, disinterested in the whole process.

Armed with a can of hairspray, starting at his crown, she backcombed his hair into a huge mass that looked like a giant explosion of tangled curls. Then, she proceeded to smooth the top back over the mess, and created a giant bouffant bubble of hair at the crown, standing three inches high. After that, she parted his hair on the left side, and teased the front lightly, so that it too stood at least an inch off the scalp. Next, she smoothed the curls at the bottom together, creating an outward flip that circled all the way around his head. Finally, she removed the two rollers in the front, and swept the lightly curled bangs to the side. There was just one more thing left to finish off the chic look she had created, so she grabbed a barrette with a yellow bow, and clipped it into his hair on the right side, next to the bangs. It was this clicking noise that finally got his attention, and made him aware that something wasn't right.

Running to the mirror, and pulling off the towel, Jimmy gasped with surprise at his new ‘do. He was now looking at an expertly sculpted bouffant style that would make any girl proud. His brown locks teased high on his head, were now looking the neatest they'd looked in months, perfectly coiffed. Examining his face, his eyes were drawn to his sudden, and very conspicuous lack of eyebrows. All that was left was a nice high arch, which left him looking even more surprised than he actually was, as impossible as that seemed. When he reached up to touch them, he noticed that his nails were somehow a quarter inch longer, with squared tips, and painted pearl pink.

Jimmy screamed, and everyone else in the house came running. First to arrive were Grandma and Susie. Once they saw Jimmy with a new ‘do, not too dissimilar from the first lady herself, they couldn’t help but crack up, laughing hysterically at the feminized youth. Last in was his mother, who at first appeared shocked, and then mildly angry. She said, "Girls, you can't seriously expect him to walk out of the house in that outfit with that hair, can you?" Amazed that his mother was on his side, his hopes raised, only to then see her smile wickedly, and hear her say, "Go find him a dress."

Sarah grabbed Susie by the hand, and in a mad dash, raided their suitcases for the most ladylike outfit they could find. The young boy stood in an almost paralyzed state of shock, while his oldest sister stripped him down to his underwear, handed him a pair of pink panties with a bow at the waistband, and said, "Go put these on." as though it was the most normal thing in the world.

Jimmy looked to his mother, hoping for leniency, but her expression showed she obviously had her mind made up, so he resigned himself to his fate. After raiding her belongings, Catherine handed him a white bullet bra. Jimmy, who was now clad in nothing but the dainty panties, sobbed "I don't know how to work this thing"

His mother stepped in and lovingly fastened the garment around his chest, then set about finding something to fill it. Catherine, meanwhile, dug out a corselet. She secured the awkward device around his waist, and tightened it as tight as it would go. Meredith filled the cups of the bra with some stockings she found in a nearby dresser, then gave him a garter belt. She showed him how to correctly wear it, and with a laugh said, "Two of these go on your legs."

Just as they finished dressing him in his foundation garments, Susie, and Sarah returned from their mission, with their arms filled to capacity. Dresses, skirt and blouse combinations, lady’s suits, and the like, were all laid out across the bed. Jimmy was subjected to trying on a whirlwind of different outfits, but no one could agree on what was best. Suddenly, as though struck by divine inspiration, Sarah said, "I think that with hair that girlishly precious, her first dress should be equally as divine; something that just screams femininity. We're definitely going to need a petticoat."

That's when they settled on a sleeveless pink number, with a scooped neckline, tight bodice, and a loose flowing knee length skirt. They decide white stockings were best, so after those were attached, it was into a white full slip, and the frothy petticoat.

"Now, sit in the chair honey, so Catherine can do your makeup." his mother said.

He felt a swell of masculine pride again, and firmly stated, "I am not wearing any makeup."

"Sweetie, we are leaving this house one way or another, so you can either do it looking like a boy in a dress, or you can go out into the world as an average young lady, who won’t attract any unwanted attention."

Jimmy’s eyes darted around the room, looking for any way out of this mess, but came up short, Hanging his head in shame, he sighed, "Alright, fine, if you think I'll look normal."

"Don't worry, little sister," Catherine said reassuringly, "you will look much better than normal."

So, Catherine began to work her magic. First, she added a little concealer to hide his small, pubescent blemishes, and then, topped it with a pale powder. just slightly lighter than his own fair skin. Next, she focused on the eyes, starting with different shades of pink and white eyeshadow to really open his eyes and make them look bigger. To add a more dramatic flair, she used dark eyeliner on the upper lids. Then, she took out what he assumed was a torture device, but was actually an eyelash curler. He was told to blink steadily, as he hoped he wouldn't be poked in the eye by the mascara wand. After she was done with the eyes, she moved onto the cheeks. Jimmy may have been skinny, but his cheekbones were not. All Catherine had to do was apply pink blush to highlight them, and give them a natural glow. Finally, she worked her way down to the lips. She started by outlining them with a pink lip pencil all the way around, drawing what she called a cupid’s bow. To top it all off, his lips were filled in with a pink lipstick, not too subtle, but not bright either. Work finished, his mother gave him a tissue, and showed him how to blot his lips.

"Still think you're just okay?" Catherine asked.

"Oh my god!" was the only thing he could think of to say. Jimmy’s gaze was fixed upon one of the prettiest girls he'd ever seen. Soft skin, luscious lips, and big brown eyes; he looked very similar to pictures he’d see of his mother when she was his age. He was looking at a girl whose number he'd kill for, and she was looking back at him through the glass.

"Well, we better hurry and finish getting dressed. We wouldn’t want to miss brunch, now would we?" Sarah said, as she held the dress open for him to slip into.

As he felt the zipper slide tightly up the back, he began to not only understand why the corselet was so tight, but also, that his fate was sealed. He could only hope to see this through, and that maybe they'd come to their senses before the day was over. With the sash tied in a bow in the back, he realized he would probably need help using the bathroom.

Susie then placed a pair of pink pumps, with a three inch heel, and little pink bows at the toes, on his stockinged feet. She took his hand and taught him how to walk. The heels pushed his rear out, and forced him to step with a girlish wiggle. After he was shown how to properly hold his arms to his side, and bend his elbow, the clumsy movements were replaced with something resembling the confident gate of a feminine young woman. "I bet you’d rather we’d be playing baseball." she giggled.

After appraising the end results of their work, Catherine removed the yellow barrette. "The color doesn't go with the overall theme, and I don't think we'll really need it, because everything else about you screams girl." she said with an obvious sense of pride.

"I was going to save these for a special occasion, and I can think of none better than a picture of my new granddaughter." his grandma said, returning from her bedroom, holding a jewelry box.

Jimmy didn't even realize she left, but now she was back fastening a single strand pearl necklace, around his neck, and clip-on pearl studs to his ears.

"Thanks grandma." he muttered, still unsure of how he found himself in this situation.

"I wore these when I was your age. It's funny how the classics never go out of style. Now, we should go down to the living room so I can get a picture of my daughter, and my four beautiful granddaughters in front of the fireplace."

Jimmy reluctantly stood for picture after picture in various poses with different family members. His grandmother said her favorite was the one of the four granddaughters laying on the stomachs, with their faces in their hands, smiling at the camera.

It almost seemed surreal, but the dream-like state came crashing to an end, when his mother announced, "Come on, ladies. We don't want to be late for brunch."

Jimmy was given a pink double breasted peacoat with large lapels, and large black buttons, as well as a pair of wrist length white gloves, perfect for a young lady. "Remember dear, a lady never ventures out without her gloves. You’ll have to wear them any time you go out when you’re older." The icing on the cake was a pink pillbox hat with a big white bow on the front pinned on top of his bouffant, and set across the crook of his elbow, a pink handbag filled with what he would need to freshen up his makeup.

"Mom please, you can't make me do this." he begged.

"I'm sorry honey, but you really need to be taken down a peg." In that moment, as though inspired by the muses themselves, Meredith said the word again, "Peg. Peggy. That sounds cute. You know, we were going to name you Margaret if you were born a girl, after all, so it fits. Come on, Peggy, it's time to go."

To be continued.

Author’s notes: Thanks for checking out part 1, y’all! The next part won’t be out for a while yet, as I intend to post these sparingly, as kind of a little treat between my longer form historical pieces. I’m currently splitting my attention between my next piece, set in the early 1980s, and my next collaboration with Nicegent, a three parter with the first dropping sooner rather than later, once I get through the back half.

Right now, available at https://www.sixpacksite.com/store/what-s-your-tale-nightinga... is my new premium story, illustrated by DreamLN01 who y’all might remember from our last project, “Mall Bratz” If you’d like to support me, and my work, please give it a buy. I’m certain you won’t regret it. ^_^ See y’all soon.