Kim To Kimberly is the serialized story of an effeminate young man trapped into a reluctant transition by his older sister and her alpha male ex-boyfriend. Chapter 3: Years after the blind date at the drive-in where he was forced to give a BJ to an older male, Kim is now grown-up but out of work, so moves in with his sister Karen. To cheer him up, she suggests he dress as Kimberly again and go out in public. She's amazed at how quickly and deeply he gets into being Kimberly with each outing and pushes him farther - finally taking him to clubs to meet men. He's confused why he likes passing as a woman up close and fooling guys, but big sister understands: he's starting to think like a female. *Just a quick reminder and request to click over to Amazon and check out my exciting, sexy two-part e-book, Born To Be A Transvestite Trophy Wife (…for my alpha male best friend!). Search for author name or title. I will be eternally grateful for your patronage and I promise you’ll love it! With appreciation, Suzi B. Queen

Kim to Kimberly
Chapter 3: Thinking Like A Female

In the years after the fateful drive-in date, Kim finished high school and went on to junior college to study graphic design. Since junior high he had often sketched and painted to fight off his loneliness, and in art school found he had a real talent for illustration. Soon he earned an associate degree in art with straight As.

He thought his social life would improve in art school, hoping that in an artistic field girls would appreciate him for his talent and not care he wasn't macho. Yet, although he would often compliment girls on their clothes or hairstyles to be friendly with them, this very behavior plus his small and fragile physique branded him as a sissy again. Needless to say, no girl would have anything to do with him romantically. He was approached several times by gay male students, but Kim just wanted to be normal.

With his AA degree and portfolio in hand, he sought work as a graphic artist. Although people were very impressed by his work, he interviewed poorly. He was too withdrawn to really sell himself and show he was truly motivated.

He could only find stock work in a department store, which he held for two years until the recent downturn in the local economy. That caused his layoff just days after he turned twenty-one, and he was forced to give up his tiny apartment. Alone and without prospects, he turned to his sister for help in turning his life around. Since their mother had passed away in the intervening years, she was his only living relative.

With her roommate Linda’s agreement, Karen let him move in with them "until you get your feet on the ground." Since he couldn't pay rent, their deal was that while he continued to look for work, he would clean house, cook, and take care of all the laundry and personal errands the girls needed done. He did his chores well and learned to keep their townhome apartment spotless, how to launder their delicates, and how to cook a few basic meals. To keep himself from going crazy with boredom, he threw himself into his chores, and even found he enjoyed doing each job well. He didn't even mind buying pantyhose or tampons. The girls were very pleased with how well he took to his domestic duties.

After six weeks with no job prospects in sight, Kim started to get depressed, and Karen grew concerned about his mental state. Remembering the fun that he had in the past dressing as a girl, she thought it would cheer him up to do it again. She always was fascinated by how girly he would become, and now was curious to see him with a grown-up look. She sometimes thought it was a shame he was born a boy, because he was too delicate and too sweet to be a boy. And if he was a girl, she thought, he’s cute enough that he’d never be lonely like he is now. So, one Saturday morning when Linda was out of town, Karen suggested that she and Kim go out that evening as sisters.

Kim was thrilled by her suggestion. He hadn't dressed since that terrible night at the drive-in but had often wished he could pretend he was Kimberly again. It had been fun and always made him feel closer to his sister. It was also a thrilling prospect to go out as a stylish, sexy young woman and not just dress at home as a teenaged girl. In addition, now that he knew the danger of attempting to pass in public, the risk factor added an excitement to dressing that he never felt before. His stomach did flip-flops from anticipation, and he enthusiastically agreed.

Karen had him shave his legs, then tried to give his shaggy hair a girlish shape. She gave him a pair of stretch lace panties and reminded him how he used to tuck himself to hide any boyish bulge. She slipped him into an A-cup pushup bra and topped off the cups with small foam enhancer pads, giving him a modest feminine bosom that wouldn’t attract too much attention. She lent him a billowy sweater with flowing sleeves and loose midriff, paired with a youthful wrap-around plaid skirt. His small feet perfectly fit into a pair of her tennies that enhanced the length of his slender legs. His eyebrows only needed some light plucking and brow pencil to give them a proper shape, and a little eye shadow, mascara, blush, and lipstick completed the illusion.

Kim flashed a bright smile at his reflection. He admired Karen's work, still amazed at how makeup could make him look so much like his sister. He liked the outfit too, still youthful but more sophisticated than his high school look for the drive-in, a cute style more appropriate for a real girl his age.

Standing behind him, Karen noted this was the first time she saw Kim really smile since he moved in.

She looked him over carefully before they left the apartment. "You look terrific, dear. You look so much older than the last time we dressed up. Remember the drive-in?" Kim knitted his eyebrows in annoyance, but Karen continued. "Wow, the back of the skirt really flatters your bottom, although it's tight in the middle. This style of sweater hides your lack of a real waist, but I’m sure you could fit into some of my dresses if you lost weight and got smaller through your middle, chest, and shoulders.”

Karen rubbed his chin. "And I still can't believe you don't have a beard,” she said. “Your smooth skin makes you look so real. You're so lucky you don't have to shave."

"I do too shave!" Kim retorted. "A little, on my chin, about once every week...or two..." his voice trailed off defensively.

"Ug! I'd hate to put a razor to my face! It's so bad for your skin, the drying, the cuts. You really should think about laser hair removal. Get that fuzz whisked away and you would probably not even need foundation."

"Aren't you getting a little carried away, sister?"

Karen shrugged. "Well, if you only have that little, even as a male you might as well get rid of it once and for all. But my point, honey, is that you look natural, not overdone like some man pretending to be a woman. Just an innocent, realistic little sister.

“You know what else," she said, scanning him up and down, "having boobs helps your posture. You're usually kind of hunched over, but now you keep your shoulders back and stick your chest out with pride." She looked him straight in the eye and said very seriously, "You should be proud of your breasts."

Something about the way she looked at him gave Kim goosebumps. Looking at his enhanced shape in the mirror, Kim had to admit that he did feel some pride in having "breasts." Feeling the snug, comforting bra, the air moving against his bare midriff and naked legs, tasting his lipstick, breathing in his perfume – it all made his heart pound with joy as they stepped out into the evening.

Karen didn't want to be too adventurous for Kim’s night out, so they just went to an open-air shopping, dining, and entertainment center to stroll and window-shop. Its promenades were dimly lit, so Kim didn’t feel too exposed his first time in public since he had been a harem girl for Halloween. His confidence in passing grew as the night wore on.

Later, he couldn't stop talking about the evening in the car and back at home. He admitted that it was thrilling to pretend he was an attractive adult female, and that tonight for the first time in his life he felt sexy. He said he was afraid to admit how much he loved dressing, but that if anyone would understand, it was his sister. And so, could they please do it again?

Kim's smile warmed Karen’s heart. It had been a long time since she saw his face so bright. The thought came to her that maybe he would be happier living as a woman, or even becoming one. She wondered if the thought had ever occurred to Kim.

He interrupted her thoughts. Two things bothered him about tonight. At one point, in the ladies' room, a woman had looked at him very critically. Kim thought that she must have been able to tell he was a boy, and it made him feel very uncomfortable.

"Of course, how could I be so stupid?" Karen exclaimed. "It's easier to fool a man, but a woman would notice the little details you're lacking. Like, look at your nails, they're so short and rough, and your skin is so dry. And you weren't wearing earrings! We'll have to work on your nails and get your ears pierced this week. I don't want you to go through that embarrassment again, dear."

Touching one ear lobe with a stunned expression, Kim nodded in agreement. Karen continued, "And what was the second thing that bothered you tonight?"

Kim broke into a shy smile. "From now on, when we go out like this, I want to pretend I’m really Kimberly, not Kim dressed up as a girl. So, can you call me Kimberly once we start getting ready and when we’re out? It will be easier for me to, you know, be her, which will make it more fun. I hope you understand."

"Of course, Kimberly, of course." Karen squeezed her brother's arm reassuringly, intrigued by his wish to take on a female persona. "And you'll have lots of fun, little sister, I promise you that. And yes, we’ll go again next week."

Starting the next day, Karen insisted Kim work on developing a realistically femme appearance. She had him go get his ears pierced, practice feminine gestures and voice at home, and work on his nails while letting them grow longer. His hair was past his ears, and Karen evened it out a bit to get it into a convincing messy bob. While in the house he was in short heels all day, all week. They also practiced enhancing his appearance with more dramatic makeup and junior-style dresses and skirts that revealed a lot of leg. "A girl has to draw attention to her best features. Men won't care if you're a little flat on top, with your long legs and cute tush, girl," she teased him.

Their second Saturday out was back at the dimly lit outdoor mall, but instead of just walk and window shop all evening, they also had dinner at an outdoor patio restaurant. Karen told Kim that interacting with the server and having a girly conversation in public was a good way to gain confidence and work on his voice and mannerisms. She also pointed out this was one of her favorite places to check out guys since it’s near the fitness center, and went on to ask her little sister’s opinions of the hot hunks as they passed by.

With this strategy, she was doing more than helping her brother play make-believe. She wanted to see what would happen if she forced him to think and form opinions about male bodies from a woman’s point of view. It was sort of an experiment whether she could influence his gender and sexual orientation. To Karen’s delight, “Kimberly” quickly fell into character, surprising even his sister with “her” keen appreciation of the males of the species. Particularly the macho, muscular type.

Karen’s next plan was an afternoon-to-evening affair so they could do some shopping before dinner. Going through several shops and boutiques would immerse Kim in a typically feminine activity, but Karen also simply wanted him be out in and interact with the world as a woman and get comfortable being seen as female. She didn’t have a conscious plan in mind, but was merely following her lifelong fascination with bringing out his feminine side. Besides, she needed a few things, so why not drag her little sister along?

In fact, day by day, Karen noticed that her brother was acting more frequently like he actually was her sister. He was more talkative, more animated than his boy self. He was happier and more fun to be with. Around the apartment, it seemed this confident, cheerful personality was starting to take over. Most striking, he seemed to more completely slip into a female identity each time he went out as Kimberly.

She was impressed with the physical change that had come over her brother as well. He was practically starving himself and taking great care of his hair and nails. His face glowed with moisturizer, and his touch at makeup became more skilled. She was amazed at how after just a few weeks of dressing up again, he had a polish to his presentation that most real girls would envy. A few weeks ago, she wondered if he would be happier as a woman. Now she was sure of it, and felt a sisterly duty to take Kimberly's personality development to the next level.

So, for their next adventure, Karen announced they were going to do something more exciting. Before she would tell him, however, she had some special dress-up treats for Kim, which she would give him when he was done showering and shaving his legs.

When Kim came out of the bathroom, Karen announced, “I have three special treats for making my little sister sexier than ever! First, new boobs!”

“Oh my gosh, what?” Kim screeched.

“Yes, what every girl wants, bigger boobs,” Karen joked. From a shopping bag, she brought out a rectangular box and opened it to reveal two realistic silicone breast forms. They were the color of his pale skin and had a natural weight, teardrop shape, and projecting nipples. Kim slipped into an underwire bra and nestled the boobs into the cups with eyes wide, then stood upright feeling his posture change, pulling his shoulders and arms back and curving his spine to balance his body.

“Wow! Your top shape is beautiful, Kimberly,” Karen said, taking something else from a drawer. “Now let’s do something for your bottom shape!”

She handed him a control garment that seemed designed for him, a firm high-waist tummy control panty with a thong back. It would narrow his middle, and keep him tucked in front without compressing his bottom. That way, in any outfit it would be as plump and round and as full as it could be.

Karen slapped her brother’s curvy derriere. “You got it, you got to flaunt it, girl.”

Blushing, Kim slipped the tight garment on, pushing his testes up and tucking his penis down. He pulled up on the waistband in the rear and wiggled his hips, letting the back strap nestle deep between his cheeks. He posed and turned in the mirror, impressed by how nothing showed in front but everything showed in back.

Karen now held up a bag from one of the mall boutiques. "Okay, sister, now that your shaping is perfect, I bought you the perfect outfit to show it off. But first, tell me: do you want to look hot?"

"Sure. What is it?"

"No, you've got to want to look really hot, and say it!"

"All right, Karen," Kim's curiosity and excitement were building. Enthusiastically he said, "I want to look really hot!"

"Ta-da!" Karen said triumphantly as she pulled a flash of bubble-gum pink from the bag. "You are going to wear your first Lycra miniskirt, Kimberly!" She squealed in delight. "You are going to be on parade, little sis! And I mean on parade, because tonight we are going out to meet some MEN!"

Kim looked at the tiny pink skirt with fear. It was so small, it would be so tight, and he would be purposely wearing it to show off his butt to attract men, to meet men.

“Oh, Karen, I like going out dressed up, but I don’t want to meet any guys,” Kim said nervously.

“Nonsense,” his sister retorted. “This is the next logical step in your adventures, of Kimberly’s, right? It’s a chance for you to learn that side of being a girl.”

Kim wondered what she meant, but in fact he was already curious what men thought of Kimberly. He hoped they noticed him, thought he was pretty, and would be nice to him if they met. Male attention excited him, and imagining himself in that skirt made him wonder how he would handle an actual encounter with one. It would be risky but exciting! And deep inside, he wanted to wear that skirt.

Taking the skirt from his sister, he pulled it up around his hips and buttoned it at the waist, then closed the disappearing pink zipper at the side. In the mirror he saw the stretch material follow his curves, flowing from his waist around the generous swelling of his bottom and pulling tight across the backs of his thighs to temptingly package his rounded girlish tush. The fullness of his cheeks made up for his relatively narrow hips, and the skirt fit well in the waist thanks to the control thong. Kim loved the smooth fit and the lack of panty lines, but was nervous about how the skirt barely covered his hips.

He proudly noted that in front the tight material showed no trace of his sissy secret. Nevertheless, he would have to be careful and keep his legs together to protect himself, but then so would any real girl, he thought.

With a pink-packaged feminine silhouette below the waist, bare-legged in 2-inch heels, carrying a little jeweled purse and wearing a floral perfume, Kim knew he looked – and he felt – very sexy. He knew that just seeing him would get a man hot and bothered.

He was nervous leaving the townhome, but grew more apprehensive as Karen drove up to a notorious "meat market” downtown. The bouncer at the door just glanced at their IDs and didn’t notice the tiny “M” for “Male” on Kim’s, then waved the “sisters” in with a wide smile.

Walking in, every pair of male eyes turned on him. Kim suddenly realized what they meant by "meat market": he felt like meat, female meat. He wanted to leave immediately, but Karen threatened to expose him unless he played along and accepted drinks he was offered and invitations to dance. Kim thought he could handle that, but was in a panic worrying that horny men would grab and fondle his bottom. In his little pink skirt, he knew his butt was bait for hungry wolves.

Kim knew he looked passable but his pulse was racing. He thought his heart would burst when two men invited themselves to sit down next to their table and bought them drinks. Kim was normally soft-spoken, but he took extra care to keep his voice light and expressive while the guys were hitting on them. Kim was happy for the drink to calm his nerves. He was relieved they didn't immediately discover his secret, but amazed they tried to pick him up in the first place. I must really look like a girl, he thought.

In a short while, Kim got over the fear of being discovered and started to enjoy the man’s attention. Just like in his adolescent fantasy, as a girl he was wanted, attractive. It was fun to finally inspire desire in someone, but he was confused about why he liked sparking those feelings in a man. One thing he did know was that fooling a guy up close was ten times more fun than just passing in a mall. By the time the evening ended, Kim couldn't wait to go back.

Karen and Kimberly went out the next night, Saturday, and both nights the next two weekends as well. Karen was responsible, but encouraged him to accept drinks and let himself go. He certainly did have a good time, and he and Karen were never alone for long.

Kim became more playful each night. He watched how girls attracted attention with their body language and how they flirted. He mimicked their techniques, especially how to show off his legs by crossing and uncrossing them. Once he had caught a man's interest, he would then play the innocent young thing. He would passively let a man guide him onto the dance floor and hold him close, as a real girl would, tolerating the flirting and touching within the limits any "good girl" would enforce.

The constant attention was thrilling. At first Kim was intimidated by being physically close to these powerful older males, and felt like he was about to be caught wearing panties in the locker room. But he learned to relax and savor the experience. In makeup and a dress, the delicate, soft spoken, pretty boy wasn't a target of bullies; he was the Holy Grail of sex all those men were seeking.

On the Saturday of their third consecutive weekend going to clubs, towards the end of the night a man Kim had been dancing with kissed him. A real kiss. They were back at the booth while Karen was on the dance floor, and the guy had his arm over Kim’s shoulder while they chatted. Kim was enjoying the close contact and it felt nice to be held, and besides that he was distracted thinking about how big and muscular the guy was. Kim hadn't noticed the man had stopped talking – Kim had been staring into his eyes in the dim light – when the guy made his move. He wrapped his arms around the frail boy, pushed him back into the corner of the booth, and pressed his hot mouth upon Kim’s.

Kim was curious and a little tipsy, but mostly afraid of exposure, so didn't resist when their lips met. Remembering his strategy in the back seat at the drive-in years ago, he tried to act as if he wasn't terrified. He let strong arms enfold him; he hugged the man’s hard body; he submitted and let firm lips linger on his soft mouth.

On the way home, Karen asked, "Well, Kimberly, did you have a good time? You were such a flirt; you had that guy eating out of your hand. You must like doing this."

Kim laughed. "Yes, but it’s confusing too. Part of me hates muscled, macho guys like that, like the one who kissed me back there, all big and strong and conceited. Fooling them is a way to get revenge on them for being so mean to me all those years. So, it’s exciting to get them revved up and then suddenly turn on the brakes to frustrate them. And it gives me an amazing thrill when they are looking right at me, or holding me or even kissing me, and they don’t know I’m a boy. But then, that’s also disturbing, to realize I’m such a sissy they can’t tell the difference.”

“You can’t blame a man’s physical instincts. That just shows how natural you are as a girl, Kimberly,” his sister replied soothingly. Hoping to learn more about her brother’s innermost thoughts, she added, “Is the fact they can’t tell you’re a boy the confusing part?”

Kim sighed. “Sort of, because when a guy is coming on to me, obviously thinking I’m real, I wish I was feeling what a real girl would feel – to feel his desire for me the way a woman would feel it. I’m confused because, why I would ever want to feel what a woman feels, when I’m not a girl?”

Karen pushed farther. "What were you feeling when that man was kissing you?"

"It was weird, because I didn’t want to kiss him – but I got excited that he wanted to kiss me. I wanted him to want it, you know? And I wanted, I guess, to let him do it. On all our nights out, I’ve only tried to get a guy interested in me just to stop him. This time, I wanted him to not stop. I wanted him to take charge of me. I liked the kiss, but more than the kissing I liked giving in to him.”

"Yes, sometimes it's fun to be ravished, up to a point," Karen replied, intrigued at her brother’s revelations.

"It's strange, isn't it,” Kim asked bitterly. ‘I’ve only been kissed twice in my whole life, and both times I was the girl being kissed by the guy! As if I really am a girl."

Karen waited a moment, then popped the big question. "Do you ever wish you really were a girl?"

"Well, sometimes, I wish I were born a girl. It seems life would be a lot simpler with a body like mine if I had the whole package,” he said softly. “And when I'm close to a guy, if he’s good looking and being nice, sometimes I wish that what was happening between us is real, and I’m real. That, like when any guy and girl meet, there was a chance we could have a future together and I could be the princess in some fairy tale with a happy ending. I know it's strange for a boy to want those things, but then I think, the feelings themselves aren't so strange.

"Am I making any sense, Karen?" he asked, exasperated.

"Perfect sense, Kimberly," Karen answered. She realized her brother was thinking like a female. A female who's ready to fall in love.