Kendra Is Born Ch. 02

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A sister builds her little brother's wardrobe.
2.2k words
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Part 2 of the 4 part series

Updated 06/07/2023
Created 01/20/2012
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komrad1156
komrad1156
3,796 Followers

As the limousine pulled into the Southcenter Shopping Mall parking lot, Kenny's heartbeat quickened. As the driver came to a stop in front of the large "Nordstrom" logo, he felt like his heart might beat out of his chest. On the way there, Kelli informed him she'd done a little bit of reading on the subject of crossdressing and learned there were specially made garments that could give a small, thin boy like Kenny an hourglass figure. She told him she'd taken the liberty of having ordered those online. Everything else Kendra needed could be found right here she assured him. At least everything she'd need to begin this new chapter in her new life once they got home and settled.

As brother and sister exited the black limo, Kelli reached the door first. Smiling, she opened it for her little brother and playfully said, "Girls first!" Kenny blushed again as he imagined himself finally looking like his older sister. Long, soft hair smoothly styled, his boyish face with "those eyes" set off by just the right amount of makeup and theclothes.Kenny felt a sudden surge of blood course through his already hard penis making it swell to capacity. "Mmmm," he thought to himself. "Pierced ears and yummy earrings! Bras, panties, slips, dresses, stockings, skirts, sweaters, blouses, and HIGH HEELS!" He felt his face flush with redness at these thoughts swirled around his mind filling him with an energy and a hope he'd never before experienced. The crushing blow of his mother's recent death seemed a million miles away—at least for now.

"You ready, baby sister?" Kelli teased again as they entered the large, upscale department store.

"I am," Kenny happily replied. "I am SO ready. Thank you, Kelli. Thank you so much. I just wanna say how much I love you."

The siblings stopped and Kelli turned to give her little brother a hug and tell him quietly whispering in his ear, "You're so welcome—Kendra. I love you, too. Now let's go shopping!"

The "girls" made a beeline for the bras and panties as Kelli explained they'd start there and work their way outward, so to speak. After they had an adequate supply of undergarments, they'd start looking for clothes, then jewelry, and finally makeup. Kenny's already long, stringy (and often greasy) hair would have to be styled, but that could wait—for now.

"Okay," Kelli said matter-of-factly. "What size do you want to be?"

"What size?" Kenny asked.

"Cup size, silly," Kelli explained. "You can be anything from a 'double A' to a 'double D' although most girls are a 'B' or a 'C.'" Kelli held up two sheer bras to show the difference between a "B" cup and a "C."

"I like the larger one better," Kenny said unable to take his eyes off the sheer white, lacy fabric. "Is that okay?" he asked innocently.

"Of course it is, sweetie. This is your own personal choice. You can be anything you want. That said, I'd have tried to dissuade you if you'd asked to go any bigger. When we go out in public, you'll have to be able to pass as a real girl and having a cup size larger than a "C" looks unnatural and draws way too much attention. This full "C" will bring you all the male attention you've been craving!"

Kenny blushed furiously again. "Who says I like guys?" he retorted with a touch of indignation.

"Well, I just assumed a pretty girl would like handsome boys. I do. Are you telling me Kendra has no interest in cute boys?" Kelli saw Kenny look down then back up. Clearly, she'd caught him off guard again. "It's okay, sweetie. You know I'm on your side. This is all for you—to make you happy. You can like whomever you like. If it's boys, that's fine. If it's girls, that's fine, too. No judgment from me. Okay?"

Kenny looked up and met Kelli's eyes. He saw her genuine care and told her, "Okay. It's just that, well, I've never sharedthatpart of my fantasy with anyone. I mean, I have no interest in boys when I'm a boy. In fact, I really like a girl I met at school. She's a senior, too. Her name is Amanda. It's just that, well, when I'm dressed up, I like to imagine being with a really nice, really cute guy who'll treat me like a girl."

Kelli looked reassuringly at him and said, "I understand. That's what every girl wants. A nice looking, polite, decent man to treat her like a princess. And if he has a big dick, well that's icing on the cake, right?" Kenny's red face turned purple.

"Kenny, we're going to have to work on that blushing. Blushing is okay for a girl, but you have to learn to control it so you can be in control of the situation. There'll be time for that. For now, let's get you the pretty undergarments you'll need. Let's see. How about white, and off-white, a black, a red, and a blue bra with matching French-cut panties? Then we can go look for clothes. I'm pretty sure you'll need a size 32 so we'll make you a 32C. And we're going to need a few strapless bras, as well so you can wear off-the-shoulder dresses and sweaters. Sound good?"

"Soundswonderful,Kelli," Kenny told her honestly. His heart was absolutely racing as this deeply-held fantasy was coming true!

After buying Kendra her first bra and panty sets, Kelli handed the bag to Kenny and directed him upstairs to find enough clothes to start Kendra's wardrobe. "Next time we do this, Kendra will be doing the shopping with me," Kelli proudly announced as Kenny smiled approvingly.

As they got off the escalator, Kelli blurted out, "Oh my God! Look! This issocute! Look!"

Before Kenny could catch up, Kelli was holding up a beautiful plum-colored knit dress with spaghetti straps and a square front that had a lacy edge to it.

"Look at this, Kenny! This issocute. Do you like it? Please tell me you like it!"

Kenny took it from her and held it up to himself unaware anyone else might even be looking. "It's perfect, Kel! But could I get it in the white instead?"

Kelli laughed. "Of course! But that'swinterwhite, not white. Girls know the difference between colors so pay close attention, okay?"

After setting aside the short knit dress in winter white, the "girls" made a whirlwind tour of the store. With just enough guidance to keep Kenny from buying things no girl would wear in public, Kelli let Kenny chose Kendra's wardrobe. All in all, he did pretty well. They found a very cute matching cardigan sweater for the knit dress, two other dresses for semiformal wear, three cute skirts, two blouses, and two beautiful longsleeved sweaters. A short black coat topped off the clothing spree as Kelli anxiously led them to look for stockings and shoes.

"We have to have the right color shoes and stockings for each outfit and you're going to need a purse that matches your shoes or that at least makes sense with the outfit you're wearing. And remember, a girl canneverhave too many shoes!"

Kelli helped her little sister-to-be select a dozen pairs of new shoes. Flats, heels, mules, wedges, and sneakers all made their way onto the checkout counter. As with Kenny's slender body, he also had small feet and was able to wear a woman's size 8. Soon, another two dozen pair of stockings and pantyhose made their way into a large shopping bag. The sheer number of bags forced the "girls" to take them to the waiting car before going back inside.

"Let's take a break for lunch and we'll finish up at the makeup and jewelry departments. Are you having fun?" Kelli asked.

"I've never had so much fun in all my life, Kel! This has been the best timeever," Kenny beamed.

"Well, just wait until we get you home and put all of this together! And then, soon, if you work hard and pay attention, we'll be ready to go out somewhere for dinner and a movie and maybe—just maybe—go dancing, too. Sound fun?"

Kenny's cock felt like it was ready to unleash a gusher of goo that would drown him in his own bodily fluid as managed to croak out a reply. "Yes, it does sound fun. It sounds like more than just fun. It sounds like a dream come true."

After finishing their orders, the "girls" made their way around the jewelry counter picking up several pairs of clip earrings until they could get Kendra's ears pierced, necklaces, chokers, bracelets, bangles, and a couple of watches and rings for Kendra to wear. Last stop—the makeup counter!

"Wait here for just a sec, okay?" Kelli asked. Before he could reply, Kelli walked up to a beautiful woman wearing a white lab coat behind the counter and began talking with her. The woman looked over at Kenny, smiled, and nodded politely. Beckoning with her hand, Kelli waved to Kenny to come over.

"Kenny, this is Chantel. She's going to color code you and help us select the right color foundation for you then build a makeup palette we can take home. Don't worry. She knows and she thinks it's fantastic I'm helping you with this. Don't be embarrassed, okay?"

The blood had long drained from Kenny's face and he replied confidently, "I'm not. Not at all. I'm very ready and very excited so let's get started!"

Chantel explained why it was important to color code his skin and why the color of the foundation was so important to present a clean, natural look. "You have beautiful skin. I'm envious. I remember when I was 18 and mine was flawless like yours. You're very lucky. I think you'll be able to use this lighter shade that will give you a China-doll kind of look if you go blonde. For now, you'll need this slightly darker foundation to work with your dark hair. Do you plan to keep your hair dark or will you be bleaching it?"

Puzzled, Kenny looked over to Kelli who said, "We haven't decided yet. I think we'll stick with this dark, coffee-colored brown for now because that's his natural color. However, I think he, well,she'dmake a very beautiful blonde, as well."

"I agree," said Chantel. "And these high cheekbones. Oh, my. Between them and these beautiful eyes. Well, let me just say, you are going to be a beautiful young lady!"

Kenny felt the blushing start again but managed to control it. "Thank you, Chantel," he said as he flicked his eyes the way he'd seen girls do. She and Kelli smiled and gave each other "that look" of approval as Chantel went on to explain the details of tweezing, shaping, liner and eyeshadow color and application, the use of blush, and finally how to apply lipstick and gloss. Kelli splurged for an expensive set brushes as she explained their importance to Kenny.

Satisfied they finally had everything a girl could need to look pretty and alluring, the "girls" headed outside to discuss their plans for Kendra's first foray into the world. A sort of coming out party for a very late but beautiful bloomer.

On the ride home, Kelli said, "There's just one thing left to do to get you fully ready for tonight. We're going tohaveto do something with that hair of yours. It's long enough—just below chin length—and it's thick enough. It's just, well it's such amess, Kenny. We can't get where we need to go without great hair. And you've got the potential. All we need now is someone to turn that potential into reality. And I know just the person to it!"

"Driver?" Kelli asked. "Take us to Aurora and 118th, please. We need to stop at the Salon Boutique!" Kelli pulled out cell phone and got hold of the girl who did her hair. She had an opening and was all-too-happy to take a walk-in.

Two hours later, Kenny had a shampoo, cut, and style that gave him the option of wearing his still-long hair in a boyish style or depending on how he parted it and combed it, in a more feminine way. As the stylist turned him around to see the finished product, the eruption Kenny'd been withholding all day gave way as felt he warm fluid escape as he looked at the soft wave of hair caressing his face. It was silky, smooth, and exactly as he'd imagined so many times before. Somehow, the mass of goo hadn't made its way through the denim of his jeans as Kelli paid and tipped the stylist.

As he slipped back into the limo, he closed his eyes and tried to imagine what he'd actually look like later that night after Kelli helped him with his makeup, clothes, and jewelry. The "stain of shame" began to spread forming a large wet area around his crotch. Fortunately, Kelli wasn't paying attention as she prattled on about clothing, makeup, and hair—and boys. Kenny's thoughts turned to Kendra as he pictured how she'd look in any of the outfits they'd just bought. That familiar swelling began anew stretching the fabric already wet with his own cum.

In Chapter 3, Kendra makes her grand appearance!

komrad1156
komrad1156
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2 Comments
rondell347rondell347almost 9 years ago
Wow, wow, instant makeover.

Brain Synapse just switch ?, Sis on a long term Hypnosis regime ?, painless move to clothes hanger.

Must need further infrastructue/friends, too isolationist by half, but then I haven't read Ch. 03, so onwards.. (4stars)

With a wry smile

MichelleWhoIsMichelleWhoIsabout 12 years ago

I waited to read chapters 1 & 2 before commenting. You have started a really fantastic story of Kendra's journey into who she really is. I loved how you wrote about Kelli's acceptance and love for her little sister. I hope that chapter 3 will be written and posted soon.

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