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.