Hello friends,

Best wishes, Suzi B. Queen

Kim To Kimberly - Chapter 5: Double Date With Danger

Double Date With Danger

Kim and Karen were just starting to watch a rom-com early Monday evening when big sister’s phone chimed. Karen picked it up off the coffee table and glanced across at her brother with an intensely amused smirk. Kim wondered who could be calling to spark that reaction. Just as she swiped right it dawned on him that it must be one of two men, and he hoped it wasn’t –

“Hello, Scott,” Karen sang, her eyes laughing at Kim, her eyebrows wiggling. “No, this is fine. Yeah, we had a great time. Michael is really interesting and quite the charmer. Thanks for introducing us, although we did meet in the one class when he had those dreadlocks. What a character!”

Kim could see the light in his sister’s eyes when she spoke about Michael as she and Scott exchanged small talk. He was happy for her but felt guilty that he might become a complicating factor in their relationship. He wanted to just disappear but knew what was coming.

“Of course! She’s right here!” Karen’s eyes grew wide with glee, then locked on Kim’s. Karen frowned as if mentally telegraphing instructions to him. In a flash it occurred to the boy that she was playing a prank, but couldn’t tell if it was on Scott, or him – or both of them? His mind was spinning. With no other idea what to do, he knew he was supposed to stay in character for now.

Karen was finishing with Scott. “I know, but I’m sure she’ll get her own when she finds a job, and then you can call her directly. Well, thanks so much, again, oh it was, definitely, of course, I will, you too, bye-bye. Here’s Kimberly.” Her eyes focused on her brother’s when she said the name, and at this point he had no choice but be Kimberly.

“Hi, Scott,” the feminine boy said when he took the phone. Kim was glad he was so well practiced in speaking like a girl that he was totally in character. “How nice of you to call,” he fibbed. “How are you?”

"Hi, Kimmie? I’m great. How are you?”

“Oh, I’m just ducky.”

“Ha ha ha. I love when you say that. Hey, I have to tell you I had a terrific time last week; it was a lot of fun. You're so easy to talk with too. It's rare to find a girl who's so sweet, and is also as cute as you."

"Oh, I bet you say that to all the girls,” Kim replied. His mind was spinning trying to think of what to say and how to act. “But...thank you for the compliment, Scott. I had a good time too. It was so nice to meet you." Karen was leaning in and listening intently as a sister would with her real sister, her face reacting to every word.

"You're welcome,” Scott said. “But it's only the truth, Kimmie. I said last Saturday that I really want to get to know you better. So, I'm calling to see if we can get together this weekend. Not a high-pressure thing – as a matter of fact I thought you and I could double with Karen and Michael and go see a basketball game. We have season tickets for the Wildcats at City Center Arena, almost courtside, and we'd like to take you girls to the game and then a nice dinner afterwards. And Kimberly, I won't take no for an answer."

"Well, Scott, thank you. That's really sweet of you. I need to check with Karen – uh – I thought I heard she had other plans. Hold on a sec."

Kim shot a panicky look at Karen and hit the mute button on her phone. Making sure the red light was on and the man couldn’t hear him, Kim said, “Oh my god! Karen, what are you thinking? As you can tell, Scott he wants to go out with – you know, Kimberly! Actually, he suggested that us two double with him and Michael at a basketball game downtown on Saturday. Says they have great season tickets down low. How do I get out of it?!"

"Get out of it?” Karen looked at Kim with disbelief. “Are you crazy? Two hunks? Successful? And I definitely want to see Michael again. Not to mention to people-watch the celebrities and style on display courtside. It will be a great chance for us to dress up with some city style, too. And this game is the hottest ticket in town! They're playing the champs – ooh, this is going to be so exciting.” Kim’s eyes popped when Karen said “going to be.” Rapidly nodding “yes” and staring at him, Karen added, “Tell him we'd love to go!"

"But Karen, what if he finds out...?"

"Don't worry, little sister. He won't find out on one date the way I’ll have you dressed, and we can cool him off later. But I want to go to the game,” she slipped into a whine, “and you're my ticket! Besides, you're lucky a man like Scott is interested in you. Any girl would love to catch him! Enjoy his attention while you can and have fun with it." Kim was trapped. He knew he had to go through with it, even though he didn't agree he was lucky to have a man chasing him. He unmuted the phone.

"Hi, Scott, uh, sorry. We just had to work something out. We'd love to go."

"That's great! We'll pick you and Karen up at your place at 5:00,” he said.

The man’s voice became softer, warmer. “I'm really looking forward to seeing you again, Kimmie. I've thought a lot about you the last two days. You're a special lady." Scott continued to chat quietly with Kim, asking if Kim liked sports, what movies he saw recently and which ones he liked, what type of food they should go for after the game.

Ten minutes later Kim ended the call and sat frozen in shock. Karen smiled triumphantly from across the room, her face red with excitement at her brother’s embarrassment.

"Well, well, well,” she chirped. “You two sound like two little love birds already. Did Scotty just want to hear Kimmie's voice?" Kim grimaced. What was he in for?

Karen jumped up and pulled her brother to his feet. “Let’s go plan our outfits, Kimberly!”

She dragged him reluctantly to her bedroom, plopped him down on the bed, and opened her walk-in closet.

“I just want to wear something loose and baggy,” Kim said. “Nothing eye-catching, but kind of anonymous so Scott doesn’t think I’m playing up to him or something.”

Karen looked dismissive. “That ship has sailed, honey. You agreed to go out with him and have to hold up your end of the bargain. And you are not going to embarrass me looking like some old maid, Kimberly,” she insisted, quickly flipping through the garments. “We meet two great guys, this is our first date with them, and you want to dress like a nun? What are you thinking, girl? We’ve got competition, Kimmie! We have to show the guys that we’re interested in them! We have to look sexy!

“And think of it from their point of view,” she added, turning to him with hands on her hips.” They want to show us off. We’re supposed to be eye candy. We’ve got to make our men look good! Oh, I know! You can build your outfit around my red leather jacket!”

“Oh Karen, that’s so expensive – and flashy. I’ll stand out.”

“That is exactly the point, sister. Duh-uh! And tight jeans, and a midriff tee, oh, and low heels. I have a pair of red heels I’ve worn with that jacket that you can borrow.”

“Jeans?! No way! Any tight pants will be even more revealing than my Lycra miniskirt, as far as my boy parts are concerned. I can’t do that!”

“No worries.” Karen waved a hand. “I know just what you need. We’ll go online tonight, and it will be here in two days. Then Kimberly and I are going shopping for jeans. We’ll go for the skinny silhouette to lengthen your legs. While we’re out, maybe we can also get you some leggings.”

“Which I’ll never wear,” Kim retorted. He was worried that he’d look too sexy in a flamboyant jacket and too exposed in tight jeans, like he’s dressing hot on purpose to keep Scott interested. Yet this was Karen’s actual plan. “But don’t you have some jeans I can borrow and we can skip the shopping?”

“Your hips are narrower than mine, so my jeans won’t fit you,” his sister replied. “You need something in a junior size that fits your hips and accents your butt, darling. But then, what sort of look in jeans? Flashy rear pockets? A pair with big brass buttons up the front to draw attention to your smooth front? There are so many options in theory, but we’ll just have to see what we can find on only one trip.”

“So, we’re going shopping, with me as Kimberly?” Kim’s mouth hung open. “Go into women-only places like the fitting rooms?”

“That’s what I said, little sis,” Karen said with a smile, coming over to her brother. She leaned down and hugged him. “This is getting more exciting by the minute. Gosh, what should I wear for Michael?” She frowned and flipped through her closet again as she continued talking about Kimberly’s look.

“For you we should look for something with a skinny leg to show off how thin they are and extend their length. It will create the right proportions under the short jacket to be a really cute look. And I’ll let you pick out a big handbag at the mall too. And . . .,” she smiled teasingly, “since I see you in a shorty tee under the jacket, you need a bra that will show the natural shape of your new boobs and even a little nipple!”

Dumbfounded, Kim watched Karen frown and put a finger to her mouth, looking him over head to toe. He had a happy rush remembering that same look from the times she would dress him as her charm school pupil when they were younger. But then he had a rush of fear realizing this dress-up episode would be on a date with a man who thinks he’s a real female. He felt light headed.

Two days later the special garment to flatten Kim’s groin enough to look like a girl’s arrived. It was another thong but abbreviated to allow him to go with a bare midriff. It was also much tighter where it counted. Karen ordered her brother a Small and Extra Small, and Kim was grateful the Small was sufficient to push everything up and in so snugly that absolutely nothing showed – because even the Small almost made him faint when he stood up and pulled it into position.

The trip to the mall to find the right jeans was like a dream for the cross-dressed boy. He was immersed in a woman’s world of gleaming marble floors and pillars, glittering displays of cosmetics and perfumes, and racks and mannequins draped in fashions of every style and color. He enjoyed how he passed as a female without notice among all the many looks of ladies out shopping. He wore a simple skirt that was easy to slip on and off, and Karen had him try on at least a dozen pair before she found the perfect one.

They were understated, a bit faded, and their snug fit in the hips revealed Kim actually did have a bit of a flared figure there. With no bulge and girlish hips, Kim looked great in front. But the best part of Karen’s selection was how they flattered Kim’s round rump and enhanced its definition with a deep center seam that split his plump globes. The overall look would make the perfect causal yet sexy complement for a flashy red leather jacket.

“Oh gawd, Kimmie,” his sister stared at him in the store’s three-way mirror, “you are going to look so hot in those with that cropped jacket. The thong means no panty lines and I think it helps define your cheeks too. Very nice! And that area where you were most concerned about the fit,” she said, glancing down at his flat groin, “looks perfect. Like there was nothing there in the first place. Okay, let’s take those up and pay, and then get you a new purse as your special treat for being a good girl for big sister tonight.”

Kim could only stare in awe at his feminine silhouette turning this way and that in the mirror. “Oh gawd is right,” he sighed. “Karen, you’re a genius!”

Saturday arrived too soon for the effeminate male. His transformation into Kimberly began with he and his sister doing each other’s nails. His turn came second, and as Karen carefully brushed a blood red gloss over her brother’s’ fingertips, she took the opportunity to plant a few seeds of feminizing thought into his brain.

“I know you’re nervous about tonight, Kimberly, since it’s your very first time going out with a man,” she said in a matter-of-fact tone. “So, let me give you some big-sisterly advice. But I have to say, going out with a successful hunky guy like Scott on your first date – well it shows you’re doing really well for being a rookie in the man-hunters’ club!” She giggled and flipped her hand.

“Am I?” the boy asked sheepishly. He felt a flash of shame, remembering how he’d pick out guys to flirt with at the clubs, rather than wait to be approached. Was he a “man-hunter”?

“Oh, def!” Karen laughed. “Anyway,” she drawled, “the other day I said you should have fun with this, and I wanted to tell you what I mean. It’s very simple, really. What I mean is, you’re going to be Kimberly tonight. You have to promise me you’ll be the girl in the couple. Alright?” She smiled at her brother like she just said the sky is blue, but he was lost.

Ignoring his confusion, she continued in a breezy tone. “One way to get in the right mind set when you’re out with a guy is to notice and appreciate the physical differences between the two of you. He’s big, muscular and assertive, while you’re small, smooth and soft. You’ll quickly realize you’re one part of a masculine/feminine couple, and you’re the feminine one. Anyone looking at you two will know who the girl is.” She stared at her brother and pointed at him. “You,” she stated. Kim thought he was starting to understand where she was going with this.

Karen continued in a more serious tone while moving on to do Kimberly’s last nail, “Once you accept that you’re the girl in the picture, then you’ll be free to fully enjoy the experience of a man treating you like a princess. Of Scott spending a pretty penny on you, driving you around in his big car, taking you to a special event, and showing you off. Now that’s fun.”

Kim squirmed a little to think he’ll soon be on display to thousands of people – as a female!

“Which brings up another important thing, Kimberly,” Karen said. “Think how important this is for him – the sport, his team, these tickets. It’s a big deal. And of all the people in the world he could have invited including some potential big client or something, he asked you, Kimberly Reynolds. Right?” She tilted her head in emphasis.

“Uh, right,” Kim answered. It felt odd to hear his full name in the female gender.

“And you need to be appreciative and attentive in response. Remember he doesn’t want a competitor, but a companion,” she asserted. Her voice grew excited. “Then – once you accept that you’re the girl and embrace your role in the relationship, and you appreciate his masculinity and generosity and enjoy his pride in showing you off – then you’ll have the most fun of all.” Karen’s eyes were wide and she locked her gaze on Kim’s as if she was trying to mesmerize him.

“Because – and this may sound weird but trust me – that’s when you’ll start getting . . . sort of romantic thoughts. You’ll start to feel the excitement of knowing you’re wanted, even desired. It’s a wonderful feeling, Kimberly, and one that only a man can give you.”

Kim’s heart pounded as he tried to fathom everything his sister had just told him about being a girl. The idea of going out with Scott was confusing and a bit scary, but now he believed it could also be nice. And after all, he would just be pretending, and just for one night.

Karen finished the last pinky and capped the bottle. “Okay, now don’t move a muscle for a bit, sweetie. It’s quick-dry but give it a minute anyway.” She smiled happily at her pretty sibling and watched a flurry of emotions flutter across his face as he thought over her advice on how to enjoy Scott’s company as a girl would.

“So, promise me?” She raised her eyebrows.

“Promise you what?” he asked back, confused.

“Promise me you’ll have fun with it, like how I explained.” She looked at him with a bland smile like it was a simple thing. “Promise me you’ll be the girl in your relationship with Scott.”

Kim was puzzled why he had to promise, but trusted big sister knew what was best for him.

“Okay, Karen. I promise,” he replied.

Soon he was taking a hot bath soaking in fragrant moisturizing oil and carefully and closely shaving not only his legs but his boy parts as well. After that, Karen did his hair with a center part to accent its length. He did his own makeup, but she suggested the darker colors he used to create a sophisticated look. Then he pulled on his thong concealer, a new sheer underwire bra that flaunted the realistic shape and nipple protrusion of his breast forms, his new skinny jeans, a snug midriff-bearing tee that displayed the womanly contours of his chest, and the asymmetrical red leather jacket. Its narrow waist flattered the proportions of Kim’s outfit and showcased his girlish hips and fleshy bottom in the jeans. As he put in his gold bangles and stepped into 2" red slingback heels, he felt very sexy but also afraid that he looked a little too hot, a little too willing.

Scott and Michael were right on time. Kim couldn't help smiling brightly at Scott as the man strode into the apartment, his chiseled pectorals outlined in his polo shirt. Scott beamed at Kimberly and took the boy's hand, towering over him. Flashing his warmest smile, he leaned down and gave Kimmie a little peck on the cheek. His affectionate touch sent a little shiver up Kim's spine, to go along with the butterflies in his stomach.

"You look fantastic! Both of you girls," Scott said. "So, are you ready for some basketball?" The girls replied enthusiastically.

"Before we go," Scott said, "show me your design portfolio, Kimberly. You mentioned you were a graphic artist and illustrator, and a woman I know may have a free-lance opportunity at her ad agency. If your stuff looks good, I'll mention you to her."

As Kim went for his portfolio, Scott checked out the sissy's girlish figure. He was pleased to see by the hint of nipple showing through the tight tee that she wasn't wearing a padded bra, revealing that she wasn't as flat-chested as he thought. He noted her long, slender legs and the smooth curves of her plush bottom in her tight jeans. He smiled to himself, knowing by the lack of panty lines that she was wearing a thong again. He wondered if the snug fit of the strap in back between those soft curves felt good to her. Maybe this innocent little girl is growing up in a hurry, he thought, and maybe I'll be the one to make her a woman.

Kim proudly showed the men his book, including designs and drawings from college and a few illustrations he did since. His mind was conflicted: he would like to get a job in the field he loved, but wondered how he could get and keep a job if the boss expected him to be a girl. Scott and Michael said he had a unique style, and thought their friend would want to interview him for the job.

It occurred to Kim how strange this was, being a girl. It seemed all he all he had to do is put on a dress and some falsies to suddenly have a rich boyfriend and career opportunities. But this also meant his situation was getting stickier – by the hour!

The basketball game was very exciting with the home team winning by one point at the buzzer. Kimmie didn't know anything about the sport, and Scott was happy to explain the rules and what was happening. He seemed quite bemused by his date's ignorance of this manly pursuit. Scott taught Kimmie to give him high-fives when the home team scored on a particularly thrilling play. Slapping his delicate hands against the man's broad palms accented to Kim how small he was compared to Scott.

Kim enjoyed this friendly camaraderie; he felt like he and Scott were buddies – and something more. Kim realized with a little shock that Scott was his first male friend. And in this alternate reality where he was Kimberly – that meant Scott was in fact his first boyfriend. His cheeks flushed as the realization hit him. Knowing that he had a boyfriend confused him, and he felt both ashamed he was such a sissy that he looked like a real girl yet proud that Scott liked him. In addition, like any young girl would, in Scott’s company he felt both vulnerable to and protected by the older male, afraid of being intimate yet intrigued by his masculinity.

All these new thoughts caused a feeling to well up from deep inside Kim, a feeling the boy couldn’t understand, something more than enjoying a friend’s company. It was a type of thrill he got from looking feminine, but it was more than the excitement of simply dressing up and passing as a girl, and more than the cheap thrill of fooling a guy and getting him to kiss you. It was the excitement of being Scott's girlfriend. Scott's very masculinity stimulated him to embrace the female role in their relationship, as Karen had predicted. It seemed so natural, he almost wished he were a girl and could further explore and experience this feeling of togetherness.

After the game, the foursome went out to eat, where the good feeling continued. Kim felt so comfortable talking with Scott that at times he forgot he was a boy. He felt like Scott's date, a girl, a girlfriend. It seemed so perfect, and Scott made him laugh so much that Kim was able to ignore the sad fact that this couldn't last forever.

Yet, sometimes when he was almost believing it was real, he would remember why their relationship was doomed and his own crazy, embarrassing role in it. He recalled the bullies in high school and wondered if Scott, nice as he was, would still lose his temper when he finds out he’s been fooled. And Kim was sure that somehow, he would find out. When that thought arose, the femme boy would lose interest in their conversation for a moment. A wave of sadness and worry would sweep over his face – before he would pull himself back into his cheerful Kimberly character. For Scott’s sake.

Then he would double down on his promise to Karen: he’d accept the girl’s role in his relationship with Scott and enjoy the man’s attention while he could. In fact, this evening was all so easy and so much fun, the feminized boy even considered that he might agree to go on just one more date, if Scott asked. But no more than that, and then he’d have Karen tell him how to break it off without letting Scott down too badly.

Despite Kimberly’s plans, it was already too late to let Scott down easy. He was quickly falling for sweet little Kimmie. He loved the music of her laughter, the gleam in her eyes when they spoke quietly together. She listened, she cared, and she appreciated the simple courtesies a gentleman should show a lady, unlike the spoiled princesses he was used to. Sometimes he and Kimmie seemed to be thinking the same thought and would make the same comment at the same time, then explode in laughter. Kimberly seemed to simply fit in with him and to complement him in so many ways. She was really special.

But he saw again that there was something that troubled her. Sometimes she'd look sad in the middle of their laughter. From time to time, he'd notice a wistful, far-away look in her deep blue eyes. It made it seem like she wasn't really there, or someday might disappear from his life without a word of explanation.

Too soon, in Karen’s mind, they were back at her place. Outside her door, the men each confidently and affectionately took his partner in his arms. As Michael kissed her and she thrilled to the sensation of having his powerful arms around her, over his shoulder she watched her brother melt into the arms of her ex.

Karen noted that Kim’s arms moved up to wrap around Scott’s neck, and saw how the man’s powerful figure contrasted with her brother’s frail body with his long, thin legs and plump bottom, and his narrow shoulders in the sexy leather jacket. The two seemed lost in the moment, and she was sure their lips and tongues were intertwined. She knew that being kissed like that after a date with a guy who likes you – the female you, that is – had to be having a more powerful effect on Kim than being kissed by some guy in a bar. But what sort of effect? She’d have to ask him in the morning.

After he dropped Michael off at his apartment, Scott drove home alone down the dark coastal highway and thought of Kimberly. There definitely was a mystery about her. Was it merely her artistic sensitivity reacting to the world around her? Was there a tragedy in her past? Or perhaps it’s that old story: a broken heart? That had to be it, Scott decided. He felt anger toward the man who would dare hurt this precious flower at the dawn of her blossoming womanhood. He vowed he'd never let that happen to her again.

He was turning into the garage at his building when a funny thought struck him. He realized that back at college Karen never mentioned she had a younger sister.

* * *