Peggy’s Night Out
By Lauren Bliss

The chauffeur pulled into Willow Haven country club, and the door man held the door for four young women as they entered the building. He noticed how they all seemed to possess a different type of beauty. A young girl in her pinafore dress with hair in tight sausage curls nearly leapt out of the car over the excitement of her first visit to a fancy social gathering. She was followed by a smartly dressed young woman in an aqua, linen suit, appearing as confident as she was beautiful. Next came a very fashionable woman in a nice floral print dress with impeccable poise. However, the last one to step out of the vehicle almost seemed reluctant to do so. She was a little too insecure, though he could not tell why. A stunning girl clad in pink and white from head to toe, almost a woman, but still young and cute enough to be quite the little heartbreaker. What he didn't know was that the adorable shy girl was not a girl at all, but rather a boy who had pushed his luck a little too far.

"Come on Peggy. I can't wait to get inside and see all the pretty dresses, and try all the little finger foods." said little Susie.

"Yes, hurry up, little sister. Mom and Grandma are waiting inside." said Sarah, growing impatient with him as usual. Jimmy couldn't believe it had gone as far as it had, but here he was, dressed like a teen queen, about to participate in the routine of polite society, and the pointless surface conversations with strangers that went with it. He was certain someone would see through his disguise, and it terrified him.

Catherine took him by the hand, pulled him close and said, "Remember, little sister, no one will see anything other than a gorgeous young lady out for a meal, unless you give them a reason to think otherwise. Just be yourself, but a more… graceful version of yourself. Just don’t forget to swing your hips when you walk."

"But what about my voice?" he asked, panicking. "Surely, someone will figure it out."

"I hate to break it to you honey, but you're not even an alto, let alone a tenor. Just speak softly, and choose your words carefully. Don't say anything unbecoming of a woman in society, and you’ll be just fine."

Their coats were taken at the door, and they were led to their table by a stone-faced man. He didn’t utter a word, until he announced their arrival in the dining area. After being seated the three older girls were brought coffees, while the youngest was brought a glass of milk. The conversation shifted from who was wearing who, to what the silhouettes would be in the coming year. All in all it was a pretty uneventful meal. Jimmy's fears started to subside, until suddenly, a hand came to rest on his grandmother's shoulder.

"Vera dear, how are you?" said a mysterious, well dressed woman.

"Wonderful Rose, just wonderful. You remember my daughter Meredith, and these are her four, Catherine, Sarah, Peggy and Susie.” she said, gesturing to everyone respectively. “They're in town for the weekend. I’m blessed to have them till tomorrow."

Rose smiled, acknowledging everyone at the table. "My, what lovely granddaughters you have. This is my daughter Elizabeth." She gestured to the stunning blonde standing by her side.

"Beth actually. I like your dress." she said, looking straight at Jimmy.

The frightened boy muttered a quiet, "Thank you." while staring down into his lap.

Meredith explained, "Sorry dear, Peggy is dreadfully shy."

"It's quite alright. She seems like a nice girl. Elizabeth could actually use a few nice friends. You know, I’ve got an excellent idea. Let me steal Peggy for the rest of the day. The girls could come shopping with me, and then have a slumber party tonight. Maybe it would help her with her shyness. I promise to have her home before you leave."

Jimmy's doe eyes practically begged his mother to save him. Unfortunately for him, he’d exhausted the last of her sympathy. She did however find the whole situation extremely amusing. She thought, perhaps this would help him learn to quit while he's ahead. "If you're sure it's no trouble I'm sure the girls will have a wonderful time." So, Jimmy left the dining room on the arm of a cute teenage dream. Only, it was not in the way he hoped his first time out with a girl would be. After retrieving his coat, he carried it draped over his forearm with his purse, since the afternoon had grown warm.

Unlike many of the other women of Willow Haven, Rose drove her own car. Her husband walking out left her with little choice but to learn to fend for herself. Even after a hefty divorce settlement she still thought it better to handle such minor things on her own. She could spend her money on other things, like lavishing her daughter with everything she could ever need, or want. They pulled into Sophie's Boutique, a stylish little shop that catered to women of all ages. Rose was looking for the perfect outfit for a date that night. She sent the girls to go find something for themselves, her treat. Beth took Jimmy by the hand and led him deeper into the store. "I can't believe she's seeing that man again. He's after her money, but she doesn't care. Whatever gets her attention, I guess. What about you? How are things your mom and dad?"

Edging a little too close to the truth, Jimmy said, "Actually, my dad died last year and it's been kind of rough. My mother, sisters, and I are always arguing with each other over the dumbest things. I know she wishes I was more like them; pretty and sweet, you know. That's the only reason I even came out today in this ridiculous pink number. My mom made me."

"So you're one of those, I’d always rather wear pants, types. You know, there are ways to wear pants and still look feminine. You can still do all kinds of things you wouldn't expect and still be feminine. I happen to think you look adorable, by the way." Jimmy found Beth’s comment strange. He knew girls often showered each other with compliments, but this was different somehow. He may have been dense, but something was off about this girl. He just couldn't quite put his finger on it. She seemed nice enough, though. He decided there to make the best of it and just get the night over with. Suddenly, Beth got an idea. "I'll pick some things for you to wear, and you pick some things for me. We can model them for each other when we get back to my house." Jimmy, having no idea what he was doing, searched the store until he came upon a little black party dress, with a built-in petticoat. He had heard Catherine say numerous times that black went with everything, so he grabbed it and met Rose and Beth at the register. The items were paid for, and the three were on their way.

Rose went up the stairs to begin getting ready for her evening out, while Beth took Jimmy by the hand and pulled him into their kitchen. "I usually make my own dinner," she said, "but tonight I think I could use some help. We’re making lasagna." She threw a pink, floral print apron around his neck to match his dress. She herself, donned a yellow pinafore with ruffles around the shoulders. Jimmy, ignorant to the ways of the kitchen, followed all her instructions as best he could, but really wasn't much help. He was starting to get the feeling that she was just happy to have someone else besides her mother in this big empty house.

With the lasagna in the oven, the two sat down to watch some evening television. A short time later, Rose descended the stairs wearing a fancy, glittering evening gown, ready for a night on the town with her suitor. "You girls be good while I’m gone. I've left some money on the kitchen table in case of an emergency. You have Jerry's number and the number of the restaurant if you need to reach me. I'll be home late. Have fun, you two." she said, smiling and waving as she walked out the door.

"I thought she'd never leave." Beth said, jumping up from the couch. She bolted up to her room with a flash. Jimmy could hear shuffling around, and a drawer opening and closing. When she returned, she carried what looked to be a poorly rolled cigarette. "Do you smoke marijuana?" she asked after she lit the joint, took the first puff, and held it in his direction.

Jimmy had never smoked anything before, but his fragile masculine ego would not allow him to admit it. "All the time," he lied, taking the joint and taking a much larger hit than he should have. After that, he started coughing as though he was choking on a golf ball. Beth watched attentively. The strange behavior of this new girl continued to entertain her. Finally, regaining his breath, he passed it back to her, and so it went for the next ten minutes or so. Jimmy felt strange, but also carefree for the first time in a long time. He found it odd that he was enjoying the situation he was in, in spite of how he was dressed.

Like a signal from the heavens, the timer went off. The two were so hungry they almost couldn't contain themselves. The dish made it onto a plate by sheer force of will and they began to dig in. Neither cared too much about manners at this point so they scarfed the whole plate as fast as possible. When they finally looked up at each other, they both laughed at the sauce smeared all over their faces. Jimmy, having no experience with makeup, wiped his mouth haphazardly with the napkin, completely ruining the amazing work his sister had done earlier. Beth took him by the hand and led him upstairs. She said, "Come on. It's time to get ready anyway. I'll fix your face.

"I can't believe my mom." Jimmy slurred. "She thinks she can have this much control over my appearance, but I’m the one who has to walk around looking like this."

"You should teach her a lesson." Beth agreed. "You should do something crazy. I have an idea!" She took off into her mothers bathroom and returned with a bunch of liquids. "Here, take off your dress and stuff, and put them in this bag. I'm going to wash your hair and we’re going to try something new."

Only too happy to obey the pretty girl showering him with attention, the intoxicated Jimmy complied and met her at the sink in the bathroom where she was waiting. Placing her baby blue, silk robe around him and covering his neck in a towel, she washed and conditioned his hair, trying not to tangle up the back combing even more. After she was done, it hung limp to his shoulders again with his bangs tickling his delicate eyebrows. She pulled out her hairdryer, and brushed through it a hundred times till it was dry, silky smooth, and straight. She coated his hair in a strange smelling liquid, carefully trying not to get any on his forehead. When she had thoroughly saturated every last strand, she wrapped his head in plastic wrap and for the second time in a day he found himself not quite alert, sitting under a drier. Straddling his lap, she armed herself with cold cream, and an array of cosmetics, all designed to take this cute girl and turn her into a sexy woman. The eye shadow was swapped for a few different shades of gray and the eyeliner was applied heavier and smudged a little. The ends were drawn out into wings to create a cat eye effect. Beth called it a smokey look. His cheeks were darkened to make them look more flushed. After lining, the lips were filled in bright red, and they looked as plump as they possibly could.

Beth finished his makeup, so she slid down to his feet and removed the stockings and garter belt. She then gently slid up a dark tan pair of panty hose in their place. Still high, Jimmy wasn't quite sure what exactly was going on. He just knew he liked it. She disappeared for thirty minutes, returning with her makeup finished, her hair up in a big French twist, wearing the dress he had chosen for her earlier, and perched atop the highest heels he'd ever seen.

After checking his hair, she decided it was dry enough so she led him back to the sink. One more round of washing, conditioning, drying, and brushing, and she proclaimed him ready to be styled. First she teased his hair at the crown. It wasn’t as extreme as earlier in the day, but she created a solid bump at his crown that finished in pin straight hair down to his back. Next she curled his bangs with a brush and some hair spray so that they rolled down across his forehead, just above his eyebrows. Finally she added a wide red headband, sitting just behind the bangs, in front of the bump, and holding all his hair backwards over his ears.

"Are you ready to see the outfit I chose for you, today?" Beth asked. He quietly nodded in agreement. She stood him up and had him step into a red dress. "You were so displeased about wearing pink today, so I thought I'd give you a chance to be the lady in red." She zipped up the back, and gently guided his feet into a white pair of platform knee high boots. Done dressing him, she walked to her vanity and collected a few things. He thought it felt nice when she rubbed a cool liquid over his earlobes, but was shocked when that feeling was replaced with a stab of a pin, followed by a sudden weight pulling at his ear.

"What do you think you're doing!?" Jimmy screamed, not caring whether he sounded like a girl or not.

She replied, "You can't wear this dress without earrings. Now quit whining. We're already halfway there." She repeated the process on the other side, balancing the look. The tugging sensation in his earlobes didn’t really hurt at all, but it reminded him that this had probably gone too far already, and there was still no end in sight. "All done!" Beth exclaimed. "Are you ready to see the final result?"

She took him by the hand and walked him over to the full length mirror. In the reflection he saw a stunning beauty wearing a red, sheath style mini dress, with huge white polka dots, and white go-go boots. Her make up was done in the sexiest way possible with alluring eyes, and kissable lips. Two red disc earrings hung from her ears. Her crowning glory was the mane of golden blonde hair that now fell down her shoulders. "Why the hell did you do this to my hair!?", he shrieked, almost crying. "It's blonde. My mom is going to be pissed."

"That was the point." she laughed, but after realizing he didn't think it was funny, she tried to comfort him. "It's going to be okay."

"It's not going to be okay. You don't understand. I'm a..."

"A what? A boy. I know."

He fell silent, stunned, and after a moment he asked "How did you know?"

"Well, I had my suspicions that something was a little off about you. I kind of thought, maybe what was off about you that is what’s off about me. I tried to confirm it by getting all touchy earlier, but instead, when I sat on your lap I found out the actual reason. It was either that, or you’re a total freak who stores half a hotdog in your panties for some reason."

"So, you're saying you like girls?"

"Well yes. I like you too. What does that say about you?." Jimmy was shocked. A girl finally had taken an interest in him, but only because he was made up like a beauty queen. She gave him a few moments to process, then Beth broke the silence by saying, "It's time to go."

"Wait what!? Go where!?"

"You can't seriously expect to get all gussied up and stay in, can you? We're going dancing. I know this great band playing downtown.There’s already a cab waiting outside. Trust me, Mom won't be back until just before she comes in to get us up in the morning. Let's just say, I don't like to give it away without at least one date." Five minutes beforehand, he never would have dreamed of leaving the house looking like he did, but he was the one grabbing their coats and tugging her out the door. Jimmy didn't understand why but he was crazy about this girl, and if this is what it would take to be with her, he would do it again, one thousand times over. The two enjoyed a lovely evening together, talking, dancing, and joking around. Beth even convinced him to dance with a boy at the show. He was okay with doing anything and everything as long as at the end of the night, he was still going home with her.

They took a cab back and found their way to the bedroom. While kissing, hugging, and cuddling, Jimmy knew that he had to see her again. It occurred to him though, that she wanted Peggy. She didn't even know Jimmy. He knew that if things were to go all the way it might destroy the illusion. They decided to just enjoy the touch of each other's skin, and they fell asleep in their undies cuddling.

The next morning he awoke to her kiss. They heard the sound of Beth’s mom pulling into the driveway. The two started to get ready and Beth removed his corselet and slip. "I got you some other clothes too," she said. "Some that I thought you'd be more comfortable in." She dressed him in a pair of black capri pants, a white, off the shoulder, angora sweater, and a pair of pink, heeled sandals. She brushed his hair back and tied it high, in a ponytail, at the crown. She removed his evening makeup and replaced it with the cosmetics found in his purse from the day before. The finishing touches were a pair of white, plastic, hoop earrings, a pink ribbon tied in a bow around the ponytail, and a pink scarf tied jauntily at the side of his throat. She smiled while looking deep into his eyes and said, "See? I told you there were ways to look feminine while wearing pants."

The two shared a laugh while making their way outside, carrying Peggy's garment bags. Peggy was wearing huge white circular sunglasses, and joking about how she looked like a movie star arriving on set, with Beth carrying her things like some kind of personal assistant. Rose stood in the driveway to greet Meredith Baker. "Thanks for letting Peggy stay over. The girls got a little carried away with their makeovers, but I was right. Elizabeth is in a better mood, and Peggy really seems to have come out of her shell. We hope to have her over again soon." Meredith thanked her and turned around to see Peggy and Beth kiss each other on the cheek goodbye.

The ride back to their home was spent entirely in silence. The family stepped through the front door, with the girls exchanging looks, wondering when their mother was finally going to explode, except Peggy, who found a spot on the couch as though nothing was out of the ordinary. Meredith took in the sight of her new daughter, looking like a blonde Barbie, ready to try out for cheerleading. Peggy looked at her mother square in the face and said, "I want to stay the night with Beth next weekend so you need to figure out a way to get me there. Also I'm going to need some more clothes since nothing I own goes with my new hairdo. You can’t expect me to visit the salon in slacks and a button down, you know." Meredith didn't know what to say. It seemed her attempt to get rid of her son's bad attitude, and lack of style had some unintended consequences. The lack of style was gone, but so was her son. The bad attitude hadn’t gone anywhere though, and Peggy was here to stay.

Thanks to the handful of folks who have been following me since over a decade ago. I see you. <3 I still intend to keep releasing these between larger projects, and the wait shouldn’t be so long for the next. I had some personal issues occupying my attention for a while, as well as finishing up my camper van. Halfway to living the dream now. :)

If you would like to support me, you can purchase any of the premium stories I’ve done for Six-pack, and others on lulu at https://www.lulu.com/search?contributor=Lauren+Bliss&page=1&...

Next in the pipeline, depending on how soon some things come together, will probably be a free illustrated story, more inline with my historical romantic fair, though set in a certain retro-futuristic world. After that, be on the lookout for part 3 in this series, “Slumber Party Trap”