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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 who falls in love with him. In Chapter One we meet the young Kim, a delicate and naturally feminine boy who is bullied by macho boys at school for being such a sissy. But at home his sister Karen dresses him as Kimberly, where he escapes from his loneliness by playing make-believe. “Dressed up, he wasn't a sissy. He was a real girl, and the object of all their desires.”
Kim To Kimberly
Chapter One: The School Sissy
Suzi B. Queen
Kim Reynolds had always been a sissy, but he was going to get much worse very soon.
He was a skinny kid, except for quite plump, rounded buttocks that were very prominent on his thin frame. His bottom was larger and protruded much more than any other boy he had ever seen, and more shapely than many girls.
His shoulders were small and his chest narrow. He was high-waisted with rather wide hips and had slender legs, long in the thigh. This graceful bone structure, together with his full, plush bottom, made him look more like an undeveloped high school girl than a teenaged boy.
He was self-conscious about his androgynous figure, but he always hoped girls would think him cute, and he would someday find a girl, fall in love, make a family and live happily ever after. Unfortunately, he usually attracted only male attention, in the form of cruel teasing. This was especially true once he got to high school, where he was called a sissy, a girl, and even Kimmy and Kimberly by the merciless boys.
These taunts always struck home with Kim, not only because he was self-conscious about his body, so effeminate compared to the hard-bodied boys that teased him, but because he was afraid they could tell he had a secret.
He was afraid they knew that he really did pretend to be a girl sometimes, and actually enjoyed it. It was just some innocent fun with his big sister, but as the other boys were maturing into young men while Kim looked like their little sisters, he wondered if his dressing up had done something to stop his growth into manhood.
He wondered if he were a freak of nature, who should have been born a girl. He even wondered if someone could possibly be "part girl." Sometimes when he was subjected to the other boys' hateful taunts, he wished he were a girl. At least then they wouldn't hate him and he would be normal, even if he wouldn't be a "he." Kim worried he would always look this way, and wanted more than anything for that not to happen.
It really began when he was a baby. His mother couldn't bear to cut his beautiful golden blonde hair until after he was three, and in his baby pictures he looked like a little girl. Strangers would congratulate his mother for her darling daughter, such a pretty little lady, and she never corrected them. Maybe she really wanted another daughter, maybe it was just an accident, but somewhere inside Kim, the identification with femininity had been established. And since his father had passed away when he was an infant, he never had a male role model.
Throughout his childhood, his only close playmate was his sister Karen, four years older. They would play dress up games, usually both dressing as ladies. Later the games changed, where Kim's "punishment" for losing was to wear a pretty hat or a dress. He actually looked forward to losing, and would sometimes suggest what item of his sister's wardrobe he would be "forced" to wear.
As he grew, he learned a lot of "girl stuff" about clothes, hair and even makeup when Karen got into her young teens. At that point, she got even more interested in transforming Kim, sometimes just to try out beauty tips from her glamour magazines. For Halloween or a show at school, or even a little skit for their mother, she would dress him from the skin out.
Kim was a belly dancer the Halloween he was nine, complete with spangled panties and a matching bare-midriff top, with flowing, see-through pants and sleeves. His mother found an inexpensive blond wig at a thrift store, and under the top he even wore a bra stuffed with Karen's nylons. It was the first time he wore lipstick, mascara, eye shadow and blush, or any type of padding, and the first time he went out in public as a girl. The amazing thing to Kim was that no one, not even their closest neighbors, could tell it was really him.
It was a revelation to the boy. Perhaps for the first time, he consciously realized he could have been born a girl. It seemed that whether you were a boy or girl was a simple twist of fate, like the flip of a coin. Kim felt good being on the girl side of the coin. Tagging along with Karen and her friends, and some boys from her junior high, he liked being one of the girls in the group, not one of the stupid and gross boys.
Passing as a girl made him feel somehow light and easy, it let him enjoy the feeling of the clothes and the pressure on his chest, and being called "sweetie" and "dear" by the neighbors at each one’s door. He knew he looked good and he felt good, but more than that, Kim just felt right. It felt natural being a girl.
Despite his excitement about dressing, around the time he turned twelve he started feeling guilty, as the differences between boys and girls became more obvious during these years. He and Karen dressed less often and only at home in private.
Although these sessions were less frequent, they were more intense. Karen called it "charm school." Kim always had to wear heels, pantyhose, panties, a bra stuffed with stockings, and a dress or blouse and skirt – never pants or shorts. His sister worked on his clothes and makeup, and trained him especially hard in gesturing, walking and talking like a girl. Karen would make him repeat over and over, "I'm a girl, I'm a girl, I'm a pretty girl," to get him in character.
Kim had fun being Karen's "little sister." Dressed up, he felt closer to her, and their mother. She knew what her children were doing, of course, and enjoyed having "two daughters" when they played this game. She worried that he shouldn't be encouraged in his femininity, and thought he would grow out of it as he matured. In the meantime, it seemed like innocent fun, and as her son was so pretty in his dresses, and so happy, she let the games go on.
Luckily for their masquerade, puberty seemed to be passing Kim by. His voice remained soft and light. His beard never really started coming in, just a few stray blond hairs. His face kept a feminine softness. With his large eyes, prominent eyelids, cute upturned nose, wide mouth and sensual lips, he looked remarkably like his sister. Karen was one of the most attractive and popular girls in school, tall and thin at 5' 8" and 120 pounds, with a 34B-22-36 figure. He was always in awe of his sister's beauty, and even when he was dressed and fully made up, he felt like Plain Jane next to her.
While other boys kept growing through their mid-teens, Kim seemed stuck in pre-pubescence. He stayed slim and graceful like the girls his age, instead of growing muscles like the boys. His height topped off at just under 5' 7" when he was fifteen, more than an inch shorter than his sister, and his last growth spurt was mostly in his legs and thighs. Being a boy, he did fill out a bit more than Karen, but his weight leveled off at just over 130 pounds.
His chest stayed narrow, which made his hips look unusually wide for a boy. It made his hips roll in a mild sashay, giving his cheeks a little jiggle with each step. With such a prominent bottom, the girlish sway of his hips did not escape the other boys' attention and was cause for further insults.
The worse time was in the locker room. His blond hair made his body look practically hairless, even under his arms or at his crotch. He didn't grow any hair on his chest or stomach. On his legs and arms his hair was fine and soft, practically invisible, and on his legs faded out completely above the knee. Seeing the other boys, he felt ashamed of his frail chest, especially the baby fat that lingered behind his pale pink nipples, pushing them out to make little cones the other boys called his "titties."
Is it any wonder he couldn't identify with the sarcastic macho boys who ridiculed him and made him feel like a freak? While they concentrated on sports and girls, Kim took theater, dance and art, and excelled at all three. He enjoyed these creative classes, and another benefit was that he got to meet a lot of girls. He found himself especially attracted to the prettier, athletic, more confident ones. His fantasy was that one of these "cool girls" would realize how nice he was and how much he admired and respected girls, and take the initiative and ask him out. But in reality, the girls just felt sorry for him. None asked him out and none would go out with him the few times he was brave enough to ask one on a date. Ridiculed by the boys and rejected by the girls, Kim thought he must be the loneliest kid in school.
But at home, Karen would comfort him, and tell him everything would be all right, someday. To cheer him up, she would suggest a little dressing up. Kim was always grateful for her kindness and caring, and dressing up became a refuge, a fantasy world where he was beautiful, popular, loved. Dressing up as a girl was a way to get revenge, if only in his imagination, on the boys who called him a sissy. Dressed up, he wasn't a sissy. He was a real girl, and the object of all their desires.
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. In Chapter Two, Karen decides to push the limits of Kim’s feminine alter-ego Kimberly, by setting him up on a double date at the drive-in with a horny college boy. Here, the sissy’s fantasy of being an attractive girl is put to the test. -- I understand that this site generally features gentler and sweeter stories, so I must say that the situation described here is not typical of my story going forward. Her dilemma here, however, does shape Kimberly’s character as she begins to doubt her sexuality and is drawn more and more into a female identity. Finally, if you like the prose, please look up my two-part e-book at the Amazon Kindle Store, just search for Suzi B. Queen. Thank you so much! ;) XOX
Kim To Kimberly
Chapter 2: Blind Date at the Drive-In
As the two siblings got older, Karen's idea of having fun with a crossdressing brother changed. Ever since she began dating, she thought it would be amusing to see how her "little sister" handled boys too. She knew he could be dressed up and made up realistically enough to fool a boy up close, and wondered if Kim would actually like it. An unformed thought came to her: if he did like it, perhaps that mean he wants to become a girl, or that he should become a girl but doesn’t know it yet. Dressing him up and setting him up one-on-one with a guy would be an interesting way to test her theory.
So, one Saturday when Kim was fifteen and Karen was in college, Karen got him to go on a double date with her current boyfriend, Chuck, who was a senior at their school, and his best friend and teammate on the football team, Rick.
She styled Kim’s longish hair, and dressed him in pink control panties and a matching A-cup bra, which she filled with little silicone inserts she called "boy cheaters." Then she had him put on a tight white midriff top, plaid miniskirt, anklets, and flats. Kim's pulse raced as he looked in the mirror. The short skirt and bare midriff made him feel very sexy. The cheaters even had subtle nipples that pushed through the top, giving him a realistic feminine look.
“Oh gosh, Karen, I love the outfit,” he gushed.
“Well, the true test of a girl's outfit was whether her date likes it,” Karen replied. “Don’t worry, though. Rick will love it when he sees the young, fresh, female Kimberly.”
As they waited for their dates, Kim's mother told them to have fun and be careful. Karen convinced her that it was just for laughs, and was going to be a very casual movie date. She promised to watch Kim like a hawk, and make sure "nothing happened." The nervous boy assumed she meant that there would be no kissing – and that was fine with him!
Looking over her pretty little boy, Kim's mother smiled lovingly and said, "Kim, you would have made a lovely girl. I never realized just how beautiful my younger daughter Kimberly truly is!" Kim's heart skipped a beat at her sweet words. That's just how he felt, beautiful.
He hoped his date would think he was beautiful, too, and he could completely fool the boy into believing he was a real girl. Kim imagined that the boy would want to hold hands in the theater, and maybe try to put his arm around the pretty boy. Kim wasn’t sure he would allow that, but really looked forward to their goodbye. He hoped he would excite the boy enough so he would want to kiss him. Kim didn’t actually want to be kissed; he just wanted the boy to want to kiss him. Kim figured he would let the boy kiss him on the cheek, or maybe he’d be brave enough to give the boy a quick peck on the lips if he was nice. Then once he was safe inside afterward, he expected to get a good laugh at the boy’s expense, thinking how the guy would be falling in love with his feminine image, never knowing Kimberly was really a boy!
Right on time, the doorbell rung when the boys arrived. Rick was several inches taller than Kim, had a broad chest and strong arms, and seemed very polite. Karen introduced him as Kimberly, and he was excited at the attention and flattery the young man paid him. Especially since Rick was the type of macho guy who tormented him at school. Kim marveled how a boy's attitude was so much different toward him when the boy thought a he was a she. This wasn't so bad, being a girl, he thought. Kim felt butterflies inside as the young man firmly took his slender hand and led him to the back seat of the car where he would soon learn that being a girl is more than being worshipped from afar.
During the ride to the movie, Karen and the guys mostly talked about the big game last week, and it seemed that Chuck had thrown the pass and Rick made the catch to score the winning touchdown. Kim really didn’t care, but played along with Karen’s subtle encouragement on how to act like a girl and made sure he showed the proper amount of enthusiasm. He was afraid he went a little overboard in his gushing praise, calling Rick his “football hero,” but Karen seemed delighted. He assumed she was pleased with his performance.
It was when the car turned into a drive-in theater that Kim got the first indication their sweet double date was more dangerous than he had imagined it would be. As soon as they parked, Karen slid over to get cozy with Chuck. She leaned her head on his shoulder, blocking Kim’s view, so Kim had to move next to Rick to see the screen. Instantly the man’s arm was over and around Kim’s shoulders, cradling the boy’s elbow in his large hand and pulling him close to his muscular chest.
Kim had imagined that Rick would be like the boys his own age who would slowly and clumsily try to sneak his arm around the girl in a crowded theater. Now he immediately found himself in the arms of creature very unfamiliar to him, an adult male, in the semi-privacy of the back seat of a large sedan. The heat of Rick’s body, his musky aftershave, his possessive attitude toward his feminine companion put the boy on edge.
Things were pretty cool that way for a while, but began to heat up when Karen and Chuck started making out in the front seat. Kim was shocked at how blatant they were. He knew Rick had to be getting ideas of his own about his date. And it wasn’t long until the man reached his free hand across Kim’s face and caressed the boy’s smooth cheek. He turned Kim’s head toward him – Kim didn’t realize why but cooperated and looked in Rick’s eyes – and then it happened.
His first kiss. He was shocked and tried to not tremble. Rick’s hard lips and trace of stubble were so strange. He couldn’t help but feel anguish that he should be kissing a girl, instead of being the girl. He was also afraid that Rick would somehow be able to tell from kissing that he wasn’t a girl. He had to act like it was normal for him to kiss a boy, and that he wanted it and liked it. The problem was he didn’t know how to kiss. He had been prepared for a quick goodnight kiss at the end of the evening, but suddenly had to deal with Rick as he hungrily worked his way across the sissy’s painted lips. Kim tried to keep calm and relax his lips a bit, pretending he wasn’t terrified by Rick’s aggressive intensity.
Kim saw a movement in the corner of his eye and in the nick of time stopped Rick’s hand from grabbing his padded chest. Without missing a beat, Rick put his hand on Kim’s thigh. His powerful hand began caressing the soft naked flesh, pushing his skirt back inch by inch. Kim understood how vulnerable a girl in a skirt must feel, but felt it had to be even worse being a boy in a skirt. He pressed his knees together and pushed Rick’s hand away again, and again, but Rick persisted.
Karen and Chuck had slid down so Karen couldn’t see them. Their noises from the front seat made it clear they were past the kissing stage. Chuck had to be sucking her nipples, and judging by her moans, Karen loved it. Kim knew that Rick had to be getting frustrated with him, with his friend being so successful. Finally, after pushing Rick’s hand away for about the twelfth time, Rick blurted out, “C’mon, Kimberly! What’s the problem?”
Picking up on the tension in the back seat, Karen’s head popped up. Kim was right; Karen’s blouse was open and she was fastening her front-close bra. She quickly arranged her breasts and buttoned her blouse.
“Hey, Kimberly, I think we need to go to the ladies’ room, little sister. Hmmm?” Her tone made it clear it was not a request. “Chuck, Rick, we’ll be back in just a bit.”
Desperate to get away from Rick and glad to be rescued, Kim happily agreed. Karen pulled him along by the hand in a stony silence. He was planning to tell Karen how upset he was to be forced into this embarrassing and potentially dangerous situation, but when they got to the restroom Karen laid into her little “sister.”
“Kimberly, you are totally embarrassing me! You’re acting like some stuck-up little prude! You know, little sis, Rick has certain expectations. He’s a college senior, after all. There’s going to be trouble if you’re not nice to him. He knows you’re still in high school but you don’t want him to find out you’re just a sophomore, do you?”
She was talking to Kim like he was really a girl!
“But I am a sophomore, Karen – hey, wait a minute.” He realized something else was going on here. “What does that have to do with it? What did you tell him about me?!”
Karen leaned in with one leg out, hand on her hip. “Kimberly, sweetie, do you really think he’d go out with a fifteen-year-old? I told him there’s two years between us, not four, which makes you seventeen and a senior. And to make certain he’d take you out, I mentioned that you don’t know much about football, but you do like football players – a lot. I said you like jocks.”
Kim was stunned. Rick not only thought Kimberly was a real girl, but an experienced, horny high school senior who goes for jocks – they type of boys who despise him! And by following Karen’s prompting on the drive, Kim had played the role without knowing it, increasing Rick’s “expectations.”
Clutching his purse in front of him in shaking hands, Kim whispered, “Oh, Karen, I'm scared. I just thought we would cuddle. What should I do?"
Karen looked into her sissy brother's pretty face. He looked like a frightened doe, with big eyes and long lashes coated with mascara. She though what a poor excuse for a boy he was, nothing like the chiseled young men that waited for them back in the car. They would never think of putting on a bra and falsies, panties and a skirt, and get in the back seat of a car to cuddle with a horny guy, to see what it's like to be a girl.
She knew the date was her idea, but the fact that Kim was willing and eager to go along with it made her think that maybe he deserved anything that happened to him tonight. But she couldn’t let him get hurt, and knew there was only one way for him to keep his secret. It also dawned that this casual date was turning into a greater test than expected of her theory about Kim’s sexuality, and a way to see just how far he’ll go as Kimberly.
Karen knew Kim had no experience with girls, so she decided that his first experience with sex would be as a girl – with a boy – and it would be tonight.
In a soothing tone she explained her plan. "Kimberly, you need to understand that he's not trying to please you, just get you hot enough to please him. If you don't want him to touch you, you have to take the initiative and touch him. Make him happy, and he'll leave you alone afterwards." Somewhat sarcastically she added, "Then you two can cuddle."
"Touch him? Make him happy? What do you mean?" Kim looked confused.
"Back in the car, when he reaches for you, just take his hands away and reach for his pants. Start rubbing him there, you know, stroking it. He'll probably come in his pants and you'll be done."
Kim’s eyes popped out in horror. "Oh my god! Make a boy come? No. NO! I couldn't do that! I'd rather die first!"
"You won't die, probably,” Karen smirked, “but if he discovers your itty-bitty secret, he's going to get really, really mad. I’m sure he won’t get physical, but you can’t stop him from spreading the news about you all over town. I'm sure the boys in your school will be very understanding about your little hobby. Think how popular you’ll be! I bet they'll all want a special date with little Kimberly!"
Thinking about the cruel boys in school made Kim go white. He'd be branded for life if this got out. They would beat him up, or even worse they might force him to do things he didn't want to think about it. He might as well die, for the humiliation he would face. He reasoned that maybe Karen was right.
"So just, sort of stroke him, in his pants?" Kim asked meekly.
"I'm sure you know how to do that, little sister," Karen laughed. "You know what feels good for a boy. Here," she said, handing Kim some tissues. "In case any gets on you, you can wipe up."
Kim felt nauseous. "Can't we just leave? Please?!"
"No! Now do what I say, or he won't stop trying to undress you," Karen retorted. She looked into her brother's deep blue eyes and softened her tone. "Kimberly, I'm sorry. But trust me, everything will be fine if you take control. Every girl has to do it for a boy sometime, and tonight it's your turn. Just remember, he's excited because he thinks you're a girl, so be a girl. You're a girl and he's your boyfriend. And you’re a lucky girl! All the other girls are so jealous of you dating a college man. Right? Adopt that mentality and you'll do just great. C'mon, let's go back. You boyfriend is waiting for you."
Kim’s heart began racing when he opened the car door and saw Rick’s arm stretched across the back of the seat waiting to engulf him. Forcing a sweet smile, the pretty boy slid across the back seat until their hips and legs touched, when he was quickly enfolded in both of the man’s strong arms. Kim felt himself being turned toward Rick, who leaned in and nuzzled the boy’s neck with his raspy cheek.
“Feeling better now?” he whispered, obviously expecting that Kimberly’s sister had straightened her out.
“Uh huh,” the youth murmured. Kim’s hands came to rest on the man’s biceps. He squeezed the muscles, and felt the force he had to control, the anger he had to avoid.
“You like muscles, I hear,” Rick said.
Kim tipped his head up to respond to Rick’s question. “Uh huh,” he began to say, but his voice was smothered by Rick’s impatient kiss. Then Rick’s free arm moved, and Kim felt pressure on his chest. Rick’s palm had pushed against his padding; if he squeezed, he would instantly know the truth. Kim had to take control – now!
He forced a smile and moved the hand away. "I'm sorry, Rick. I get a little tender there, y'know, at that time of the month," he whispered with a pleading smile. Rick’s chest deflated. Then Kim did something he never imagined he would do. He tenderly kissed Rick right on the lips. Then, as Karen had instructed him, he reached across with his left hand and laid it on the older boy's crotch. He felt the bulky, coiled manhood start to awaken at his touch. His eyes grew wide.
"Hey, now that's better, honey," Rick hoarsely whispered. “I see you like what you found.”
He pulled back a little, letting Kim’s head rest on the man’s upper chest, tipped down. Now Kim was forced to watch himself slowly rubbing the man’s groin, rather awkwardly, with his palm, trying to not actually handle it with his fingers. He almost felt like crying as it stretched out to point straight at him. Rick moaned with pleasure. Although Kim was disgusted at the chore he was performing, he figured he had better make Rick feel good to get this over with as quickly as possible.
Kim wondered what a girl would do at a time like this, and figured a girl would respond to her boyfriend's enjoyment by getting into the act. A girl would think this was great and do something like – he reached his hand down between the man's legs to feel the shape of his weighty testicles, caressing them with his fingertips. He moved up to check the result – oh, my! – then caressed the lengthening tool with his fingers, tracing the outline of the older boy's excitement with his fingernails. Forgetting himself, Kim became hypnotized by its growing size and firmness. He gave it a squeeze at the root, then a few more, moving up toward the head. He wondered how it could still fit inside his date's increasingly tight pants.
"Hey, you're really into this," Rick whispered, giving Kim a quick peck on the cheek. “I know what you want.” Then, as if it was a prearranged signal, he called to his friend in the front seat, "Say, Chuck, I think it's your turn to, uh, go for some soda and popcorn." He sounded insincere, as if this was a signal between them.
"Sure thing, buddy,” Chuck quickly answered. “C'mon, Karen. I want to check out their arcade, too."
Karen was nervous about leaving Kim alone with an aggressive guy like Rick, but decided that their absence might spare him some embarrassment while he brings his date to orgasm. "Cool!" she relied. "Let's go!"
"B-but..." Kim stuttered and he started to sit up to stop Karen, but couldn’t move. Rick's arm had a vice-tight grip around the little transvestite’s shoulders, while his other hand had quickly moved to hold Kim’s forearm steady, keeping his pretty date’s hand gripping the bulge in his pants. Kim's heart leaped into his throat. This wasn't the plan! He was trapped!
As she slid over to the driver’s door, Karen was dying of curiosity to see what was happening in the back seat. "I guess we'll be a while. Have fun, you two!" she chimed, turning around. She had expected to see Kim facing forward and awkwardly reaching sideways across Rick’s lap, and was shocked to see how affectionate toward Rick he looked, nestling in the man’s arms. Also, he didn’t seem at all upset to be left alone with Rick, because he didn’t sit up or make any move to stop her. He didn’t seem embarrassed to be playing with Rick’s package either, because he didn’t move his hand the slightest when she turned around.
Kim was really getting into this, she thought, not knowing her brother was being held motionless. Maybe this proves he’s really gay, she mused, and his true nature is just coming out. Maybe I’m doing him a favor by getting him into boys. But a doubt still lingered in her mind – it was too dark to be sure, but was that a look of fear in his pretty eyes?
Chuck was calling her to come along, so she absolved herself of all guilt for whatever may happen to her brother, blaming him for being such a sissy. Then the car door slammed, leaving Kim alone to deal with a man with an erection.
"Alright! Now we have some privacy. Let's try this," Rick said, loosening his belt. Kim was terrified just by being alone with his date, and the guy was already undressing! The boy’s heart was racing and his head started to pound in panic.
"Unzip me," Rick ordered. The pantied boy didn't know what to do except play along. Caught up in the demands of his assumed role, he submissively obeyed. He managed to unbutton the waistband, slowly pulled the zipper down, and opened Rick's pants. Kim watched in awe as the young man pulled his cock out through the fly in his boxer shorts, revealing his arousal in the dim light. Kim couldn’t take his eyes off his date’s manhood. He became dizzy with fear and thought he might pass out.
Seeing Rick’s hard-on was a revelation to Kim. So, this is what men are like, what the boys at school are like when they get hard, he thought. He felt jealous; he was puny compared to them, but more importantly the sight crystallized his fear of them. If they found out about tonight, his life would be hell. Earlier he had imagined this date would be on his terms, but now it was on their terms – all the boys that had teased him. Pleasuring Rick would be like paying homage to all the locker room studs. But Kim knew he had no choice now; to complete his chore he had to actually touch it.
"Go ahead, Kimberly, I know you want it," the young man said. Almost in a trance, Kim reached over to take the naked flesh with both hands. His hands encircled the shaft, and he was surprised at how big a man’s cock actually got when aroused, as every girl discovers at her first encounter with one. The sissy boy slowly began squeezing, fondling, stroking it with his soft hands. He had done this to himself a few times, and now felt disgusted and humiliated to be doing another boy’s dirty work.
Yet as the older male grunted with pleasure, Kim began to understand the power a girl has over a boy. He figured Rick would like it if he quickened the pace a little. He felt a bead of moisture on its tip, and rolled it around the head with his thumb. He smiled at the man’s moan.
"That's nice, Kimberly, you sure know what you’re doing. Now, go down," Rick whispered.
"Go down? What...?" Kim wondered what he was doing wrong.
Rick chuckled. "Go down. You know, use your mouth, darlin'."
Kim was shocked at the suggestion. "I don't know... I never tried that before. I…I don't think so," he said timidly. He hoped Rick would understand and back off. Yet he knew it was something girls did for their boyfriends. His “boyfriend” thought he "wanted it." Would he act out of character if he didn't "go down"? Would Rick get suspicious?
"You never? I thought that’s what you wanted,” Rick insisted, his eyes locked on Kim’s eyes. “I can’t believe you’re a senior and you haven’t done that yet. C’mon, Kimberly, you’ll be so awesome. You’re such a loving person. And I really like you too, Kimberly. You're really special. You'll like it, too. All girls like it, especially when they swallow. That’s best for me, and it won't mess your clothes up that way, either. Chuck says your sister does it for him – don't you want to be like big sister? Come on, I can tell you'll be great! You obviously love cock."
Kim was following along but was mortified at Rick’s last words. Just because as a boy he knew what felt good, he had inadvertently made Rick think he “loved cock” so much that he wanted to “go down” on one – but never in his life had the boy even imagined such a thing. Yet now it was a reality. The notion was worse than the most terrifying nightmare Kim had ever had. But Rick had established his expectations and Kim would have to submit.
Kim felt sick to his stomach, but strange thoughts came into his head, alien thoughts for a boy. If girls like it, how bad could it be? Would I really be good at it, like he said? What does it taste like? But Kim's boy-self fought back against this bizarre temptation.
"No, not tonight. I'm sorry, maybe next time," he pleaded.
“Oh, c’mon, Kimberly,” Rick was getting upset. “You can’t leave me this way. You were so hot for it a minute ago, I thought that’s what you wanted all along!” He was definitely angry now. “Kimberly, you were the one that started stroking me! Don’t be a tease!”
Kim felt pressured to do it to keep his secret, but also had to admit that Rick was right. This was his own fault for trying to fool the young man, and he was just getting what he deserved. Rick didn’t deserve to be teased and then denied his pleasure; he couldn’t help his feelings, his desires. His very masculinity demanded from Kim a feminine response. If it was something a girl would do in this situation, he had to do it too.
The pounding in Kimberly’s head became worse, and a spasm of nausea twisted his stomach. He felt like a trap door had opened under him and he was falling, hopeless. He realized that he really had no choice and that in a matter of moments….
The thought of having a cock in his mouth was so frightening that Kim's mind would not accept that he would be used in this way. Recoiling from the shame, he wished that just for tonight he wasn’t himself – and then something clicked in his mind.
This whole scenario was too horrible, too shameful to be happening to Kim, so it wasn't. It was happening to Kimberly. Which meant it wasn’t humiliating. Rick would never get turned on by a boy, only by a girl. This macho football player would never pull it out for a boy, only for a girl. Kim knew that he would never want to do this, but a girl would – so I’m a girl, Kimberly thought. I’m Rick’s girlfriend.
In the back of his mind, he knew he was pretending, but once this switch flipped in his mind, Kimberly experienced new emotions welling up within him. He was overwhelmed by a sense of obligation to Rick, and that he shouldn’t be a tease. Then he felt like he was melting inside, that his body and mind were surrendering to the older boy's sexual power. He became weak in the presence of true virility, yet at the same time was flattered and excited. It seemed a privilege to be responsible for Rick's arousal, to experience this intimacy as a girl. It was like he was a secret agent, learning what only girls learn about boys, back seats, and hard-ons. A wave of tenderness and caring toward his date came over Kimberly. He wanted to be every bit the girl he had to be to make his boyfriend happy.
As his thoughts focused, Kimberly noticed that he had never let go of Rick’s penis and never stopped caressing it. And now it was time to go down on his date.
“Don’t tell my sister, okay?” he pleaded, looking up at Rick. “I don’t want my mom to find out.”
“Oh, I won’t tell a soul, Kimmy,” Rick lied, grinning, knowing he had made another conquest.
Rick guided him down off the seat. The skirted boy’s bare knees hit the carpet and his dream of being Kimberly really began. Like in a dream, he was perfectly calm in spite of his terror. He found it interesting that the man was basically fully clothed – easier to cover himself up if we get caught, Kimberly thought. It was strangely exciting to think that, on the other hand, anyone would know why he was on the floor of the car, kneeling between Rick’s legs.
The older male’s hard-on was inches from his face. Rick’s manhood seemed so enormous up close, standing upright like a proud soldier. It loomed even larger as Kimberly leaned forward, then it disappeared as he tipped it down and opened his mouth wide. Kimberly’s eyes focused on the boyish blue plaid of Rick’s boxers as he lowered his head, as the underside first brushed against his tongue, as his lips closed around the warm cockhead.
To take the very core of Rick’s masculinity inside his own body stunned the boy. He felt utterly defeated, yet warm feelings toward his conqueror rushed up within him. He felt Rick playing with his hair, tucking some stray locks behind his ears. He glanced up at the man; their eyes met. “Good girl,” Rick murmured. Realizing he wouldn’t be groped while he was doing this, accepting that Rick saw only a girl, Kimberly began to feel confident, in control. I’m a girl, I’m a girl, I’m a pretty girl, floated through his mind.
This idea freed Kimberly to fulfill his role more completely – to add a new dimension to the dream. Subconsciously, acting like a girl who felt affection or even passion toward her man was the best way to deny the shame he really felt. It also sparked a fantasy in the sissy’s mind. This wasn’t rape, it was romance. Kimmy did this for Rick every week. They had been dating for months, this is how she held on to her college man, her football hero, and all the other girls at school were jealous because Rick was such a jock and so well-endowed. Moving his mouth around the man’s warm penis, Kimberly said to himself, This is my prize, my candy. I love Rick, and I love doing this. I obviously love cock.
As the fantasy grew more intense, and as he got used to having Rick inside him, Kimberly’s feminine desire to please Rick started to blossom. He made his mouth water to make the cock more slippery; he began taking it deeper; he started using his tongue. He noticed when Rick would suddenly gasp, or when the man’s hands or muscular thighs would tense up when he did something that must have felt really good. In response, he started to build a rhythm around these special touches. He even tried a little extra head bob with a tongue swirl that made Rick’s leg spasm – like a puppy when you scratch his tummy, Kimberly thought.
Kimberly was so proud that his man was so entranced, so intoxicated – with me! – that he didn’t realize that his extra effort was building up the intensity and volume of Rick’s impending orgasm. Rick was panting now, completely lost in sexual abandon.
"Oh, gawd, that's great, oh – yeah!" To Kimberly's dismay, his boyfriend started to orgasm, his hips bucking upward, great gobs of seed spurting into the boy’s mouth. It was thick and slimy, salty and sweet. He knew he had to take it all to avoid a big mess. He braced himself and held his head still to let the hot jism fill his mouth. He tried to swallow it all but some dribbled out around his lips and onto his chin.
Slowly the torrent of sperm subsided, but Kimberly wasn’t sure he could stop. He resumed his sucking, his tongue action, his swallowing until he had it all and Rick began to soften. When the man was finally spent, Kimberly was grateful for the tissue Karen gave him to wipe his mouth. Strangely, his first feeling afterward was not a boy's relief that his ordeal was over, but girlish pride that he had made his boyfriend so happy.
Yet the fantasy was over. The pantied youth sat up on the seat, ankles apart, knees together, arms crossed over his queasy stomach. Rick was still leaning back with eyes closed, his breathing slowly returning to normal. Finally, he sat up and arranged his clothes.
“Kimberly, I can’t believe how fantastic you were,” he said. “That was, so, so great – and you never did that before? Well, you must have been thinking about it for a while. I thought I was in heaven. That was the best, ever!” He leaned over and kissed the youth firmly on the cheek. "Let's go to the snack bar. You can go fix up your lipstick," he said.
He kept his arm around the stunned boy’s shoulders while they walked. On the way he whispered, "That was really great, Kimberly. It was awesome. I could tell you really got into that. You were almost as excited as I was!" Then he leaned down to softly kiss his date on the temple.
Kim's head spun. Did he act as if he enjoyed doing that? Like he was excited? He knew he had to do it, but why did his boyfriend – this guy, rather – think he liked and wanted to do it? He knew he had to do it, but did he have to do it so well? Had his actions betrayed feelings he didn't know he had? Is that why he felt glad that he had made his boyfriend happy, like a loving girlfriend would?
In the restroom, real girls came and went behind him or refreshed their makeup beside him, while Kim stared at himself in the big mirror, trying to accept what he had done. Here he was, a pretty boy in girl's clothes, rinsing another boy's seed off his teeth.
When he left the restroom, his “boyfriend” was waiting with his hands holding a tray of popcorn and sodas. Kim slipped his arm inside Rick's, feeling his hard triceps through his rough cotton shirt. He was glad for Rick’s strength and support as they went back to the car, because his knees were shaky and he felt a little faint.
Back in Chuck’s sedan, they shared their snacks and watched the second movie. With Rick’s strong arm around his shoulders, Kim rested his head against the young man's chest. Karen was right, Rick wasn’t physically aggressive once he had sex. And so. Kim could get what he wanted and expected from Rick: a warm, romantic feeling, the feeling a girl wants to have with her boyfriend. He felt at peace while they ate from the same box of popcorn. Strangely, he felt a sense of belonging to, and possessiveness toward his football hero, his Rick.
His romantic mood also made it easier to accept, and finally return, some soft kisses as the evening wore on. Earlier tonight it was gross to feel another boy's lips on his, but after their intimacy it seemed a small thing. Kim felt he couldn't refuse. It also seemed a sign of the older boy's gratitude, and by looking at it that way Kim soon got to enjoy it. After all, he was pretending they were boyfriend and girlfriend, and as they made out he willingly opened his lips to Rick's probing tongue.
But back at home after the boys dropped them off and Kimberly did give Rick that peck on the lips – plus some tongue – he felt terribly guilty about what he had done. He confessed to Karen that he "went down" on his date, that the older boy said he "loved cock."
Instead of offering her brother sympathy, Karen made it worse. She said he really didn't have to do that and that a girl always has the right to say no, and that the fact he did it meant he must have really wanted to do it all along – which means he probably does "love cock."
Her words, fueled by her guilt at enabling her brother’s humiliation yet by echoing what his date had said, hurt the boy deeply. It made Kim doubt his sanity – or at least his sexuality. He felt so bad that he vowed to never let Karen make him go out with a boy again. And as the last years of Karen's college career took more and more of her time, she moved into a dorm at school. Their childhood dress-up games ended after that night.
But Kim didn't grow any more macho than he was, and the cruel boys continued to tease him throughout high school. In the meantime, Karen's idea that Kim's first sexual experience would be as a girl rather than with a girl was having its effect. The locker room atmosphere became worse, as the memory of that night made Kim feel even more different from the other boys. He caught himself looking at their bodies, comparing them to his one-time partner. He remembered the taste of sperm. He couldn't even stop thinking how Rick had been his "boyfriend," the thought Karen had planted, which added to his humiliation.
Sometimes in the locker room the macho boys would talk about their exploits with girls. Since Kim had no experience with girls but did as Kimberly, he couldn't help but picture himself in these stories – as the girl. Over the weeks and months as each bragging jock told his story, in time Kim was forced to fantasize about having sex with every one of them, and doing for them what he did for Rick. He was mortified. He learned that he had given his boyfriend a "blow job," which, on a first date, was something only an "easy" girl would do, a girl that "loved cock." It stung to think that he was probably the subject of a boys' locker room story himself.
He was still attracted to girls, but his “boyfriend” was even invading his fantasy life. It would happen when he was imagining being alone with the prettiest girl in class, kissing her full lips, feeling her soft hair tied up with satin ribbons. He would unbutton her blouse, and cup her luscious breast in her lovely lace bra.
Then, at the peak of his excitement, he would wonder what it would feel like to be her, to experience Rick unbuttoning his blouse, to feel the man’s strong hands caressing his breasts in their satin cups, inching into his bra to play with his puffy nipples. Imagining he was the girl in his own fantasy made him feel more disgusted with himself. He felt branded inside for making that one mistake, for being so good at playing dress-up that he had to suck a cock.
(to be continued...)
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.
Kim To Kimberly
Chapter 4: “Kimberly” Meets Scott
One evening early the next week, Kim was sitting on the living room couch when Karen walked in.
“Hey, little sister,” she called out, “are you ready for another fabulous, feminine adventure this weekend? I’ve got something special in the works.”
“I’m not sure, Karen.” Kim answered sadly. “It’s been really exciting dressing up, and I love how realistic I can look. It’s fun to fool the lunkheads, too. But acting like a girl with them is getting too real for me, which means maybe it’s time to stop.”
Karen sat next to Kim and took both his hands in hers. Concerned, she asked, “I don’t understand. You’ve been a real flirt, it’s true, but you’re just having fun. What’s the matter, sweetie?”
“Well, I’m a little over it, fooling the macho guys. They’re jerks, but maybe they still deserve a chance at a real girl. It seems unfair.”
“Ha! So, you think you’re unfair competition to real girls!”
Kim blushed. “That’s not what I meant,” he laughed back. “For one thing, I shouldn’t punish them for things other guys did to me. I’m starting to feel sorry for the poor dears! They seem so – hungry, I guess. I’m wasting their time.
“Second, it’s because of what I’m starting to feel when I sense their hunger for me. Last week when I got kissed, I let him do it because he made me feel special. It was almost like I had feelings for him. A girl’s feelings. It was so confusing, and it frightens me. What if I get to like this little game too much? What if one time I lose my head and let the guy I’m with go too far and – remember the drive in? I don’t want to do that again! I better stop before I get myself into trouble.”
He shook his head. “Maybe it’s time to start getting back to normal and find work.” He pulled a lock of hair and looked at the back of his hands. “It’s funny. I’m starting to think that since I’ve lost so much weight, my hair is so long, and my nails are so nice that it would easier to get a job as Kimberly than Kim right now. I better get a haircut and some protein. Get into a gym.” He lifted his arm and tried to make a muscle. He frowned.
Karen merely grinned at him. “Well, Mr. Gym Bro, before you go off and get all macho on me, can I keep my little sister for at least one more week?”
“Oh, right. You said something special came up for this weekend. What’s going on?”
“You’re going to enjoy this so much, Kimberly,” his sister said, emphasizing the name. “It will be your chance for you to sear something really dressy. I recently got back in touch with a friend from college who suggested we meet for some cocktails and dinner Saturday night at a very upscale restaurant. There’s one more coming who I think I might have met before, but I’m not sure. So, it’ll be just the four of us for a quieter weekend than you’ve had lately. More of a social event.”
Kim’s eyes were wide. “But do you think they’ll believe I’m a female, being up close and personal with them for an extended time?”
“Yes, I do. I wouldn’t suggest it if I didn’t have all the confidence in the world in you, dear.” She squeezed his hands in encouragement. “You’ll do fine, and you’ll have fun. I promise.
“And,” she continued, “because you’ve lost so much weight around your middle, I have most wonderful dress for my darling, demure little sis to show herself off in,” she sang out.
Kim couldn’t wait for Saturday to arrive. It would be fun to go out on the town looking truly ladylike in an elegant dress, especially for the last time he’d be Kimberly. His excitement rose to a new level after his shower that afternoon, when Karen threw a towel around his shoulders and grabbed some scissors. In a few moments she had trimmed some rough edges off his unkempt mane to give it a truly feminine shape, then pinned it back while allowing a few dangling locks. It made the boy’s heart race to see himself crowned with a female hairstyle and soft curls that framed his cheekbones and accented his oval-shaped face.
He slipped on his concealing, high-waisted control thong and sat down to do his makeup. He was getting quite skilled at it by now, and at Karen’s direction created a more subdued and subtle look than he presented at the meat markets. Then, while still at the vanity, Karen handed him a package of pantyhose from a very expensive brand.
“You’re going to love these, Kimberly,” she said, remembering to use the feminine name once her brother had started his transformation. “They’ll make you feel sexy from the skin out.”
Kim slipped them up his smooth legs and stood up to wiggle the top over his hips. They were sexier, silker than any hose he had worn before, and he was thrilled at knowing they were just part of the sophisticated look he’d present that night.
“Oh, my gosh, Karen, these make my legs tingle!” Kim waved his hands in excitement.
“Now let’s get your top shaped up,” his sister said, handing him a full-coverage underwire bra. She watched her brother hook the band around his waist and spin it around, then snuggle the breast forms into the cups, pulling some soft flesh into the middle to let them settle into a natural silhouette on his slender chest.
“Your dress will look better with some compression on top, so I’m going to put it on the last hook so it stays in place and tighten those straps for the look I want,” Karen added as she made the adjustments.
Then she brought out the dress. Kim’s eyes popped open at its luminous silk and shimmering embroidery. It was sleeveless with a high neck, snugly tailored at the bodice as Karen had mentioned, all in deep sky blue and featuring a brilliant gold dragon rampaging over the top with its tail curling down one hip and across the flared skirt to the other. Kim’s heart skipped a beat while Karen stood behind him zipping it up as he felt the dress tighten around his modest curves and watched his female image take shape in the mirror. He felt a rush of gratitude toward his sister for letting him experience this.
Karen suggested his accessories, choosing understated amethyst bracelets, dangling bead earrings, and a single ring on his left index finger. After stepping into matching gold slingback heels, Kim felt more feminine than he had ever imagined he could. He admired his sister’s good taste and stared at the lovely – if disbelieving – young woman in the mirror. Karen stepped forward next to him, smiling with pride at her creation.
“Thank you for letting me experience this, Karen,” Kim gushed. “Why are you so good to me?”
Karen reached across her brother’s slender shoulders and pulled the feminized boy to her side. Her voice was passionate. “I love my little sister!” she said with a sigh.
Kim sighed back, staring at himself with a dazed smile on his pretty face. “I feel so wonderful. It’s like magic. It’s going to be really hard to stop doing this, Karen.”
“Yes, it will be, Kimberly,” Karen replied with a sly smile. “Yes, it will.”
Ending their embrace, Kim – now feeling completely like a Kimberly – picked up a coordinating purse, dabbed on some perfume – a different scent from what Karen was wearing – and clicked along behind his sister as they left the apartment. He never felt more girlish, prettier, or more confident.
He imagined the evening ahead with great anticipation. Instead of the high-pressure, sexualized atmosphere of the meat markets, he would be able to enjoy a more relaxed event with Karen and an old girlfriend from school and her friend. Those three would carry the conversation while he went along for the ride, a pretty and pleasant companion there to fill out a foursome of elegant ladies out to dinner.
Kim was dazzled by the elegant ambiance when Karen pulled up to the valet parking at a swank resort hotel in Bayport Beach. He was hit with a series of quick impressions – the shining marble entry, the smartly dressed people passing in and out, the young hunk rushing to open his door. Keeping his knees together, he pivoted and rose into the warm air, feeling the breeze caress his legs in the silky hose and under his dress up to his hip bones. He had to repress a shiver at the feminine sensations sweeping over him.
His sister joined him and took his arm. They strode into the entry toward the restaurant.
“Gosh, Karen, it’s like I’m in a fairy tale,” he said.
Karen squeezed his arm and squealed girlishly. “Ooh, yes! I know just what you mean! But which one of us gets to be Cinderella?”
Kim was thrilled to that she acting like he was her real sister. His heart racing, they turned into the restaurant. A cute young woman at the podium grabbed two menus and stepped out to greet them. “Good evening, ladies. Table for two?”
“Actually, we’re supposed to meet someone at the bar,” Karen replied.
“Of course,” the woman answered, waving her hand that way. “Enjoy your evening.”
In the low light Kim scanned the room for two women dressed up in fancy outfits like he and Karen were, but apparently, he and his sister were there first. At the low tables along the side of the room there was a group of six around one and two couples talking quietly by themselves, and at the end of the bar were two young men in sport coats and open-collar shirts.
Trained by Karen these past weeks in man-watching, Kim quickly categorized them. On the left was dark, muscular, a strong jaw, intelligent eyes, not a lunkhead but really built. A Tarzan. On the right was taller, sandy hair over his forehead, easy-going expression, wide shoulders. A Surfer.
The pretty boy was startled when Tarzan seemed to look right at him and a smile spread across the man’s face. He elbowed his friend just as Karen sang out, “Scott!”
Kim was dazed. This was a completely different situation than he expected. Two women might ignore him, being lower in the pecking order, but two single men, never. He gritted his teeth and smiled to keep a sudden surge of nerves under control. He knew he would quickly have to figure out what to do and how to act to pass as a girl under their up-close inspection for the next couple of hours.
The four converged; Karen hugged Scott Kirk, the Tarzan. Scott introduced his pal, Michael Kean. Karen introduced her little sister Kimberly, first to Scott, who smiled brightly and gently squeezed the boy’s offered limp hand for several long seconds, then to Michael, who clapped two large paws around Kim’s small hand with a friendly grin.
The next hour and a half was mostly a blur to the feminine male. The guys shepherded the ladies to seats around a low table. A server appeared; white wines for the sisters and refills for the gents. Drinks quickly came, and a toast “to us.” Kim caught his sister’s eye and made a scared face before he took the first sip; she only smiled calmly in return.
Kim’s mind was spinning, but the scene soon became clear to him. Scott had dated Karen in college. Now he was setting up his best buddy with her. Karen must already be interested to agree. Kim understood he was only here for company for Karen, but also saw that this situation could easily become very complicated. What if the two of them start seeing each other? Will he get mad and break it off when he learns the truth about Kimberly, although their relationship was truly meant to be? What a tragedy! Yet he was certain that if the two did get together, she couldn’t hide his real sex from Scott and Michael forever. When the truth comes out, what could Karen possibly tell them to explain why her brother goes out in public as a convincing woman?
Tonight, however, Kim had a more immediate issue to worry about. What if Tarzan gets interested in little sister?
To Kim’s relief, the other three went off into an excited conversation about college, remembering odd professors, big games, and the like. Their chatter continued after they were seated at their table and through dinner. Kim was grateful he could get by with an occasional laugh or comment. The guys seemed satisfied to merely learn that Kimberly is an aspiring illustrator looking for work. Time flew by, and Kim finally found himself walking out of the restaurant next to Scott, while Karen and Michael went a few steps ahead, laughing like schoolkids. The boy was glad the stressful evening was ending, when Michael suddenly stopped and turned, pointing toward the lounge where music had begun.
“Hey, I just remembered they’ve got a DJ starting right now. Let’s extend this delightful evening, shall we. Do you ladies dance,” he asked with a knowing smile.
“Yes! That will be fun,” Karen exclaimed without consulting her “sister.” Kim knew she wanted to spend more time with Michael, even though that would entangle him and her further in this crazy scheme. Neither he nor Scott could refuse them, however, so the perfumed youth was trapped as Kimberly for a while longer.
They found a table near the back where it would be quiet enough to talk, but as soon as the four got there, Karen and Michael gave their drink orders to Kimberly and Scott and hit the dance floor. Oh great, Kim thought, I’m left all alone with Tarzan.
Already, the man's eyes seemed to be boring a hole in the pretty boy. From his time at the clubs, Kim recognized that Scott was becoming attracted to Kimberly, which started a wave of panic to rise inside him. Despite his fear, Kim decided it would be suspicious if he didn't get friendlier with Scott, or the man might wonder what's wrong. He’d have to act like a real girl. After all, he was supposed to be a real girl, a girl who hoped her future included a man. What better type of man than a tall, dark, muscular – and successful – guy like Scott? He had no choice. He didn’t want to, but he knew he had to flirt with the older male. First, however, he’d have to overcome his nerves.
The waiter brought their drinks, and Kim eagerly took a swig of his wine. He glanced at his nails, they looked fine. He felt his ear and made sure his earrings were still in place. He hoped his boobs were on straight. He took out his compact to check his makeup. Everything looked perfect. Well, here goes nothing, he thought, time to start being nice.
He took in Scott’s imposing figure. It occurred to him that Tarzan looked pretty good in that jacket. He reached over and rubbed his manicured fingertips over the fabric, wondering if his hands looked as shaky as they felt.
"That's a handsome jacket, Scott,” he said. “I love how there's so many colors in the fabric, but it’s so subtle."
"Thank you, Kimberly. You know, I'm very glad to make your acquaintance this evening. And I’ve been meaning to say you look lovely."
Kim felt himself calming down at Scott’s words, but it was more the way he spoke them that had a soothing effect on the boy's raw nerves. The boy -had been hoping to avoid Scott’s attentions, but began to feel at ease with him. The man was being quite the gentleman, so different from the meat market lunkheads and locker room jerks.
"Kimberly," Scott continued, "I can't help notice you seemed a little ill at ease just now. I hope everything's alright."
"Oh, everything's just ducky," Kim replied. The sound of Scott’s voice was almost mesmerizing, like he was wrapping the boy up in a warm blanket. Relaxing further, Kim's smile opened up and he turned toward Scott. He looked into the man’s eyes, which seemed very kind. Yes, this is going to work out, he thought, everything is going to be fine.
Scott took a long look at Kim, and smiled. He leaned in and spoke in a confidential tone.
"You don't do this very often, do you? I mean, dress up like this and go out?"
Kim was almost floored. Scott knew he was a boy! His mouth went dry but he maintained his composure just enough to ask, "What do you mean, dress up? Like what?" He forced a smile.
Scott’s face was relaxed. "The flashy dress. Deluxe resorts, fancy restaurants. Now, you look wonderful – sensational, actually – but it seems to me you're not so girly-girly as you appear tonight.” Kim’s blood pressure jumped up. Scott continued, “No, you’re more of the natural type, not so vain, like most other women I meet. Too much makeup, too much jewelry. I like your style better. You have a sort of innocence, a sweetness that I find attractive.
“So, what I meant to say was, I guess you don't get all dressed up fancy and go to nightclubs all the time."
Knowing Scott hadn’t “read” him, Kim sighed in relief. On the contrary, he liked Kim's style! Kim stammered back, "Th- thank you. For the compliment. You're right, I'm not used to this. Actually, I'm very nervous." Kim wasn't lying.
Scott chuckled and softly rubbed Kim's smooth cheek. "You don't have to be nervous with me, okay, Kimberly?"
Kim smiled and shook his head in agreement. He did feel more comfortable now. As a matter of fact, a sort of happy glow was coming over him. Scott made him feel special; the man seemed to truly like Kimberly as a person. And since Scott liked his girl self, for the first time in Kim's life he was glad he was so feminine. It seemed strange to him, but he wanted to be feminine – for Scott.
"You know, Kimberly – may I call you Kim?" Scott asked.
Kim felt a strong urge to let Scott use his real name, as it felt more honest. Then he decided to stay en femme. "Well," he said smiling, "you can call me Kimmie."
"Okay, Kimmie. That sounds so sweet." Scott turned up the wattage on his warm smile, and Kim wondered why his heart started thumping.
"Like I was saying, the whole ‘meat market’ scene doesn’t interest me.”
“Oh, I know what just you mean,” Kim blurted, shaking his head.
“Yeah, right,” Scott replied, nodding agreement. “I'm more of an old-fashioned guy. I want one love for my life, and I want to settle down with her and raise a family."
Kim sighed at the romantic scenario. "Yes, Scott, that's what it's all about. It would be so great to find that one special person, and make a life together. I think it would be wonderful to have kids, too, maybe three or even four. With more kids there’s more love to go around."
Scott was amazed that any modern woman would admit she wants kids, and a big family at that. Most only want to have one baby if that – as if a child were the perfect lifestyle accessory. But here was a very attractive young lady who felt the same way he did about children. He had almost given up on finding one. Could Kimberly be the woman he was waiting for?
"Gosh, that's just how I feel, Kimmy. More fun and more love. It's terrific that you feel that way," Scott answered. He looked into his companion's deep blue eyes. "I think that making a family is the perfect expression of true love between a man and a woman," he added.
Scott’s expression told Kim that this conversation wasn't just theoretical – Scott was talking about him in particular. Or “her” in the man’s mind. It was too indirect to be just a pick-up line, and it was far from being an actual proposition, but Kim knew what he meant, and knew he meant it sincerely.
He was a little flattered, until he saw himself as Scott saw him and pictured what Scott imagined the two of them doing in bed as man a woman. The sissy suddenly felt uncomfortable, intimidated by Scott’s manly presence. He remembered the locker room and the drive-in. A hot blush rose to his cheeks. He wondered if he would ever find a girl who would do that with him, who would love him for what he was. He looked down and smiled sadly.
“Yes, true love is so precious.” he replied. “I'll always believe in true love, although I know I'll never find it."
Scott’s eyes narrowed in appreciation. This girl has really got her head on straight, he thought. He also figured that when he mentioned making a family and true love, her blush was a good indication that she was still a virgin too. Karen must have been keeping her little sister in a convent. But her last comment made Scott think that there was a sadness, a depth to her character behind the innocence. There's more to Kimberly than meets the eye, he thought.
"What I like about you, Kimmie, is that you don't play the little mind games, like other girls, to impress a guy. You seem sincere, genuine." Scott flashed that smile again, and Kim felt a tug at his heart. For a second, he wished he were genuine – a genuine female.
"Gosh, I don't know what to say,” Kim answered. “That's very nice of you, Scott. I guess I am a little naive, about men, I mean."
Scott patted him on a stockinged leg, where the skirt had fallen open to expose Kim's thigh. Kim took a sharp intake of breath at the tingle of Scott’s touch on his silky hose but, like a real girl would, accepted it and smiled.
"You just stay that way, Kimmie,” Scott insisted. “I don't want anyone to spoil you. Except, maybe me," he grinned. He held out his hand. "Would you like to dance?"
Scott had always considered himself a connoisseur of feminine beauty, and on the dance floor he took stock of Karen's little sister. She was a cute, leggy kid and had a heart of gold. She had a sweet face although her eyebrows were a bit heavy, but her eyes were large and a deep shade of blue, framed by luxurious dark lashes. She had soft, full cheeks and high cheekbones, and a little chin that completed the delicate oval of her face. Her lips were a bit thin, but her smile was wide and bright. She had Karen's turned-up nose and little ears. She obviously wasn't used to wearing makeup, because her look was a little simple, but maybe with too much blush.
Her body was thin, and Scott noticed that she had to be a little flat on top. She must be a little self-conscious about it, too, judging by the high neckline on her dress and because she must be wearing a padded bra. He could tell that because there was no outline of a nipple on her bosom and it didn’t jiggle when she danced. She didn't have a lot of curves, and was a little heavier than her sister in the upper body, neck and face. She wasn't really used to high heels, either, judging by her occasional awkwardness. Her shoulders made her look a little boyish, but her voluptuous derriere above her long legs was certainly her sexiest feature.
In spite of her naiveté and inexperience, Scott knew she still had a sexy streak, because the lack of panty lines meant she was wearing thong panties. Scott smiled imaging Kimmie's sweet bottom, clad only in her thong. Was it black? No, red! he decided. So, there are some girly-girl things that innocent little Kimmie enjoys! Scott concluded that she was a real doll, and if she lost that baby fat and polished her image, she would be a total knockout.
They danced together several times, and during the slow dances Scott held Kimmy firmly, confidently, without the sneaky grabbing like other men. Kim appreciated being treated like a lady. Back at their table, Kim was surprised how easy it was to talk to Scott. He made Kim laugh, and was nice and polite. He was very concerned when Kim explained how hard it was to find a job in graphics, and said he wished he could help.
During their last dance, Scott saw she was staring into his eyes. As he returned her affectionate gaze, she smiled sweetly in response. Scott knew that Kimberly was a very special girl. He wondered if he were falling in love. Then, just as that thought came to him, a dark cloud crossed Kimmy's face. Her smile faltered, her eyes looked away from his face, a look of sadness swept over her. The man felt a surge of concern for this darling creature; he wanted to protect her from whatever that hidden pain inside her was, this intruder into their beautiful evening. He wondered what her secret could be.
Scott had never met a girl like her. She was like an angel that had come down to visit from another planet. But she's an artist, Scott reasoned, they're more natural, not always trying to be glamorous. Perhaps that also explains her mood shift. And it would account for her naiveté – artists look at life from a unique perspective, not being wrapped up in social conventions and trendiness.
When they sat back down, Scott took Kim’s hands in his. “Kimmie, I’d like to get to know you better. Can I see you again some time?”
Not being a real girl, Kim did not see this coming or know how to handle it. His conscious mind knew he was playing with fire, but the desire to have this warm feeling again overwhelmed him. Before he could stop himself, the words came out on their own.
“That would be great, Scott,” he replied. He regretted it as soon as the words left his mouth. He hoped that Scott didn’t really mean it and would forget about Kimberly by morning.
On their way home, Kim expected Karen to tease him for being the object of Scott’s attentions. But Karen was interested in the effect of romantic attentions from a real man on the development of Kim's female persona, and wanted to encourage it. She reasoned that nothing would make Kim more girlish than that special experience, even more than being the object of random guy’s lust at the meat market. She spoke to him as if they were real sisters.
She began by talking about Michael and that she always liked the surfer type, she was impressed with this technical expertise, and how they both loved bicycling. She mentioned that she gave him her number, and that they might go bike riding at the beach soon. Then she talked about how Scott had always been a real gentleman, what a hunk he was, and how successful he was in his new start-up business.
Along with a few gentle questions, her sisterly sharing got Kim to open up about Scott. Completely in his Kimberly character, first "she" gushed about how good-looking Scott was, and how great he looked in his jacket. She said that although Karen liked the surfer type, she preferred guys who were tall and dark with wide shoulders, but not muscle-bound. She loved the way Scott made her feel, like she was the only girl in the room, how he seemed genuinely interested in her as a person, he treated her with respect, and he was thoughtful and caring. Playing make-believe but still speaking the truth, she said she never got along so well so quickly with any guy before.
As they discussed the two men, Kim almost felt as if they really were two sisters talking about their new boyfriends. He was glad Karen didn't tease, because he really liked Scott, as a friend. But in this lovely dress, feeling like a fairy tale princess, it seemed natural to talk about Scott like a prospective boyfriend, and to express the girlish feelings and impressions the man stimulated in the boy’s imagination.
Eventually Kim fell quiet, and Karen noticed tears running down his cheek.
Shocked at this sudden change in Kim’s mood, she asked, "Kimberly, honey, what's the matter?"
"Oh, Karen. This can't be happening! It can't. I can't believe it!" He took a tissue from the center console and dabbed at his mascaraed eyes.
"Kimberly, what's wrong? Didn't you have a good time? You liked Scott, didn't you?"
"Scott is wonderful. It was fantastic, the way he made me feel. Like I was special. He liked me for myself, at least my pretend self, not just because I was the nearest available female. When we danced, it wasn't like with other guys, who just wanted a feel. We really danced, one of my hands on his shoulder, one hand in his, and he was leading me around the room.
“So, there I was, dancing backwards, and he was so gentle, but masterful. He's a terrific dancer, and I felt like I was floating. Then I thought to myself, this can't be happening. Everything can't be this perfect, and I can't be enjoying it so much, being waltzed around the room in the arms of a tall, dark, handsome man.
"It was like we were standing still as the room whirled around us. I was staring in his eyes and I thought he must be the most handsome man I've ever met. And then he smiled as if he could read my mind, and I thought, 'If I were a girl, I would be falling in love with him right now.' "
Karen wasn't sure if she was with Kim or Kimberly now, whether this was make-believe girl talk or something deeper. "Now, Kim, eh, Kimberly, sometimes a girl's imagination...."
"It wasn’t my imagination!" Kim retorted. He continued in a flat, emotionless voice. "Right when I thought that, about falling in love, a voice came to me, inside my head. It was so loud it blocked out everything else, every thought. It said, 'You can't have him. You're not what he wants!' "
Karen was silent. She didn't know what to say or do, except wait for Kim to continue. His voice became more emotional, almost desperate as he went on.
"Karen, I don't want a man, a boyfriend, but when I realized that I can't have Scott I felt like crying and running out of the lounge. When that voice said that he doesn't want me, it felt like a knife in my heart. It's so sad that I'm not what he thinks I am. It feels so terrible, because what might have been so beautiful – if I were a girl – was and is a complete dead end.
"But the worse part was – is – I'm frightened that I care about any of this. Why should I care? Why should I feel responsible for his future happiness? He never said he wants me, he never said he loves me, and of course he doesn't even know who I really am. Or what I am. So why do I feel like I'm letting him down? Why should I feel sad that I'm not a girl because I can't be – his girl?" His voice was shaking now. "Why does it hurt?”
The boy's bottom lip was trembling as he fought to regain his composure. His voice became a flat monotone as he continued. "And now he's going to call me and ask me out, so I can go through this pain again. It's so wonderful to be with him. But it's so sad."
Karen stared ahead at the road. It seems like her "little sister" had fallen in love, just as she had predicted. And now her heart was broken, and it was all big sister’s fault.
Back at the bar, Michael joked with Scott. "Hey, I guess you like the young ones, Scott."
"She is young, but such a sweet kid."
"Well, she does have a real fine ass, boy." Michael laughed and punched his buddy on the arm. "I knew you would go for that! You've always been an ass man."
"And her legs – long and lean. Mercy!" Scott laughed and signaled for two beers. "I'm calling her next week. She's really a nice girl. I never met a girl like that before – you know, artistic, unpretentious. She's what I call genuine."
"Well, her big sister impressed the heck out of me. Brains, beauty. Say, buddy, why don't we take the girls to the basketball game next Saturday? It'll be a good way to get to know them better."
"Sounds like a plan, Mike. Gosh, the two of us dating sisters. We haven't done that since, what, high school? Let's drink a toast – to the Reynolds girls."