Marilyn's Impossible Dream, or She's So Pretty -- Chapter 19

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Marilyn's Impossible Dream, or She's So Pretty — Chapter 19


By Katherine Day


(Copyright 2010)


Merritt Lane McGraw feels he is a girl, but he is living through the Great Depression and World War II. It is a period before the words “crossdresser” and “transgender” were in the vocabulary and a time before sexual assignment surgery was a possibility. How is this lovely boy going to survive this?

(The Story Thus Far: Born out of wedlock in 1929, Merritt Lane McGraw has spent nearly all of his first five years with his mother while she worked as a live-in maid and nanny for a wealthy young widow and her two daughters. Merritt’s mother, Evelyn, found herself in a torrid love affair with Viola Buckner, her employer, while the women’s daughters loved to treat Merritt as a little girl. Merritt was becoming more and more like a girl. To escape the demanding sexual encounters with her employer (which Evelyn feels is sinful) and to take her son away from the feminine atmosphere of the estate, Evelyn left the Buckners and returned home to live with her parents. She soon married Bob Casey, the library clerk and former high school classmate, and they have moved into a second floor apartment above a craft and sewing supply store. Merritt’s days of enjoying “girl time” appear to have ended now that there’s a man in the house.

(Merritt’s stepfather has gone off to war, and was killed in the terrible battle of Tarawa in November, 1943, posthumously being awarded the Navy Cross. Merritt’s mother meantime has taken a job in a war plant making parachutes, and Merritt takes over her dress-making business, which he finds to be a natural fit. Now a high school student, he finds comfort only in being a girl, but still seeks to fit in as a boy.

(Merritt has ventured out as a girl, and his natural femininity attracts the eyes of high school boys as well as a high school girl, with whom he goes to bed. Their innocence — typical for youth of that period — makes for limited sexual experiences, but with much passion, girl-to-girl.

(Yet, he tries to fit in as a boy, believing his hopes of ever living as a girl in the 1940s and1950s would be nearly impossible. His joy in being a girl seems limitless. Merritt finds his attraction for the girl to be growing, but she has rejected him as a boy. His sorrow over losing her is mitigated by the romance of his best friend for ‘Marilyn.’ His adventures continue. )

Chapter 19: School Days

His eyes were still red and his face flushed when he awoke the next morning. His mother had tried to comfort him after he ran off to his room, but she could do little to end his sobbing. His fragile body shook in the depth of his sorrows.

“Honey, you have school today,” his mother said, her voice soft and caring. She had gone into his room to awaken him. “Now let's get up and get a nice shower, and clean up your face after all that crying.”

“Oh mommy,” he said, holding back on what he feared might be another crying spell.

“You're so young yet, honey, and your heart is broken, but there'll be other friends for you.”

“No there won't,” he protested. “She was so special. There'll never be another like her.”

“Well, maybe she'll still like you. Give her time to absorb it.”

“Oh mommy, but she loves Marilyn, and I'll never be able to be Marilyn,” he said. “I'll never be a girl.”

Evelyn held her son tightly, finally he seemed to settle down. “Now let's get you ready for school. OK?”

“Yes, mommy.”

*****
To make matters worse,
that morning he noticed the fuzz on his cheeks was becoming heavier; he had seen the fuzz growing denser, meaning, he was certain, he'd have to start shaving. He was getting a beard, it was obvious, just like all the other boys, only his seemed to be coming a bit later in his teen years than many others. Nonetheless, it was growing.

There also was some light hair emerging on his chest and arms.

He was becoming a man. It frightened him, this prospect. How could he be a man? He was so much a girl in his mind.

*****
“Do you think you could wear my sister's stuff?” came the question from Billy Johnson.

Merritt and his friend were huddled in the cold, having gone outside for the lunch hour from West High School, and trekked along the icy sidewalks, sliding and laughing to the Terminal Square, a major intersection with a few shops, including a news vendor who sold snacks. They shared a five-cent Hostess Twinkie package, each taking one of the Twinkies.

“I think so. She's about my size, and not too big in the chest.”

“Cool, on Saturday, I want you to try on her prom dress from last year,” Billy said. “She looked so 'hubba hubba' in it.”

“I remember, Billy. You showed me a picture of her in the dress. She was so pretty.”

“Oh, and you'll be even prettier, Marilyn,” Billy said, using his girl's name.

“Not so loud,” Merritt warned. “Don't want these jerks to hear that.”

“OK, then you'll come Saturday? As you promised?”

“Yes, about 3 p.m. OK?”

“Good, both my mom and sis will be gone.”

*****
That afternoon, Merritt was called out of geometry class, and told to report to the Miss Henningson, the counselor.

“I'm afraid we can't accommodate you on your request to be enrolled in the home economics classes,” she told Merritt.

“Oh? Why is that?” he said, showing disappointment.

“Well, as I told you, we've never had a boy in those classes before, and you might cause a disruption.”

“Me? I won't cause trouble.”

“I know you won't, Merritt,” she said, showing sincere interest in his situation. “You've got an excellent record here at West, and I checked at your junior high school, and you were excellent there, too.”

“Then why?”

“The other reason, and the main reason,” she explained, “Is that some of the classes will be dealing with subjects that only girls should hear, like female hygiene.”

“Oh I know all about that,” he said. “My mother explained that all. I know what girls have and what they do.”

The counselor smiled. “I'm sure you do, but some of the other girls maybe embarrassed by your presence when those topics come up.”

“Then I'll have to take shop classes and drafting?”

“Yes, Merritt, and you'll do fine there,” she said. “You might just enjoy them.”

“I guess,” he said. He rose to leave, but she beckoned him to sit back down.

“Now, are you sure you want those secretarial classes next semester?” she asked.

“I think so,” he said, after a short hesitation. “I need to learn something like that to get a job.”

“You're wise, Merritt, but you may be the only boy in these classes. Does that bother you?”

“What can I do about that? I guess I'll have to accept it.”

“OK then, I'll set up your tentative schedule then and we can talk again.”

“Thank you Miss Henningson.”

He left the room, both disappointed; yet, he felt somewhat relieved since it might have been so difficult being the first boy in school history to take home economics. Everyone would look at him as sort of weird, he felt, but he knew he would have loved being “one of the girls” in the classes where he'd no doubt shine with his already honed skills in sewing and cooking. Still, there were his secretarial classes in the future, where he might be the focus of attention for his girlish ways.

*****
When Merritt was in a classroom, or doing his homework, he felt so safe and happy. He loved learning since it involved his mind and prompted his curiosity. He particularly liked history, constantly wondering what it would have been like living in the 14th Century among the Medici’shfg or in ancient Rome or Greece, perhaps enjoying the circles of young scholars around Socrates.

It was in the hallways, the cafeteria and the times before and after school where he found trouble. Boys still heckled him, calling him “sissy” or “queer” or “fairy” or “homo,” the favored terms of the era for suspected homosexual boys. Worst of all was gym class where the need to strip and change into his gym outfit, thereby exposing his puny body and undersized piece of manhood, always opened him to wisecracks, and sometimes even physical bullying. In the class itself, his physical weakness was demonstrated, where he was always among the last chosen in any competition.

There was no way to be excused from gym, which was held three days a week, and he vowed he'd stick it out as best he could. Merritt was learning how to endure through all sorts of shame and humiliation, just to prove he could survive.

As the 10th grade year continued, Merritt surprised himself -- and maybe even some of his tormentors -- by showing unusual skills dribbling and passing the basketball, and soon was pleased to find himself chosen by some of the better players for pickup games. To be sure, when he was involved in the pushing and battle for rebounds, he was easily pushed aside by the stronger boys, but he had an unusual ability to scoot around opposing players or keep the ball while dribbling.

“You handle the ball very well, Merritt,” his gym teacher said one day as he was leaving the locker room headed for his next class.

“Thank you, Mr. Lawson,” he replied, surprised that the gym teacher, an older man who was slender and balding. The teacher looked unprepossessing, almost meek, but in his gym clothes, the teacher showed strength in his sinewy arms and legs.

“You're very graceful, and you show good coordination,” he continued. “Let me ask you something.”

“Yes, sir?”

“Have you played tennis?”

“Yes, a little,” he said, remembering when he and Donna Mae used to go to the Humboldt Park courts when they were in junior high school.

“I'd like you to try out for the tennis team this spring,” he said.

“But, I'm not very good,” Merritt replied, appalled at the thought of competing in anything athletic. “I've only played with a girl.”

“That doesn't matter, Merritt. I think you could do well.”

“Anyway, we're beginning to hold some tennis lessons on Saturday morning in the gym, and I'd like you to attend.”

“Me?”

“Yes, and there'll be no charge,” he said. “I'm the tennis coach you know, and I'm looking out for talent. I'm trying to build a team.”

“Really, Mr. Lawson, I suppose I could try. I'm not sure I'm good enough.”

“Good, we start next Saturday at 9 o'clock. I'll give you the details Friday. See me after class then.”

“But I work on Saturdays,” Merritt said, remembering his work at Swenson's.

“Maybe your employer will let you come in a bit late. The class is only an hour, and we have tennis equipment.”

Merritt nodded, and hurried off to his class. He was both excited and scared; never before had he been praised for having any athletic talent, and here was the coach inviting him to try out for the tennis team.

“Hey Donna Mae,” Merritt yelled at his friend as she went through the alley behind the store on the way home. He had planned to stop her before she got home from school, and found his timing was perfect, getting out into the cold just as she entered the alley from the Bennett Street entrance.

“What Merritt?” she stopped.

“Wait up? Need to tell you something,” he said, running to catch her, his breath crystallizing in the frigid air.

“Hi,” she said, as he reached her.

“Remember when we used to play tennis?” he asked.

“Sure, a couple of years ago.”

“Well, Coach Lawson wants me to tryout for the tennis team this spring, and I don't think I'm good enough.”

“You were getting better each time we played,” Donna Mae answered. “Why does he think you could make the team?”

“You always beat me,” he said. “And you're a girl and I don't think he was recruiting me for the girl's team.”

“But you really were getting better, Merritt,” she said. “I had trouble beating you the last few times, you'll remember.”

“I guess I could learn,” he said. “They're beginning tennis lessons Saturday and he wants me to go.”

“Do it, if you can. You've got good coordination.”

“That's what Coach Lawson said, and he said I'm graceful.”

“Well, that you are,” she said with a smile.

Donna Mae said she was going to be on the Our Lady of Angels Catholic Girls' Academy, tennis team this year and indicated that once Merritt got through his tennis lessons, she'd love to beat him again. They both laughed.

*****
“You're so pretty, Marilyn,” his friend Billy said on Saturday after Merritt had put on the prom dress that Billy's sister had worn the previous year.

It had taken Merritt nearly a half hour to change, putting on the panties, bra and dress, along with fixing his hair and applying makeup and nail polish. Merritt wanted to look so beautiful and girlish for his friend that he was careful with each detail. He had prepared a pair of firm sponges the size of a B-cup breast for himself, and once stuffed into the bra filled him out as a lovely, well-formed teenage girl.

“Come on, Marilyn, hurry up,” Billy yelled through the door of the bathroom where Merritt was changing.

“I wanna be pretty for you, Billy,” he yelled back, his voice squeaking a bit. “It takes time for a girl to get ready. Don't you know that?”

“Oh I know, but I wanna see you.”

Finally, Merritt emerged, wearing the green halter dress, which exposed his almost dainty shoulders and thin arms. The dress was cinched at the waist, but flared out, ending just above the knees. Merritt wore no hose, since it was still in short supply due to wartime shortages, but had put on a pair of open-toed sandals with three inch heels. His toe nails were painted in a light pink tone that matched his lips. The sight was of a wholesome, girl next-door type, since Merritt had understated his eyeliner and shadow and his soft color on his lips. He was able to brush a slight bob to his longish hair, and fix a small bang on his forehead

Billy, who was waiting anxiously, leaped to his feet, hugging Merritt firmly, but avoiding kissing the lovely girl in his arms.

“You are prettier than my sister was,” he said. “She'd be so jealous.”

Merritt relished the moment in his friend's arms, at that moment feeling as if by magic he had become a complete girl in a half hour. He relaxed into the hold of this tall lanky boy, felt the boy’s larger hands caress his arms and wrap themselves around his shoulders.

“I want to show you off to the world, Marilyn,” Billy gushed. “I'll be the envy of every boy in school.”

Merritt accepted his friend's words as sincere, since at the moment he felt nothing other than a pretty girl. He turned his head up, as gave Billy and short kiss on his lips.

“What do you want to do now?” Merritt asked, finally breaking loose from his friend. They had settled on a couch, and Billy continued to place his right arm around Merritt's shoulders, while the other hand caressed the lovely girl's thighs.

“What does a guy do with a pretty girl?” Billy asked, quickly answering his own question. “Let's dance. I've got some Glenn Miller records and someone all you girls like -- Frank Sinatra.”

Billy went to the combination radio-phonograph console, lifting the cover on the large piece of walnut furniture, and placed a 78 rpm record on the turntable. He placed the needle on the record, and in an instant the familiar strains of “Stardust,” a popular Hoagy Carmichael piece, filled the room.

Merritt settled into the grasp of Billy, resting his head on the boy's shoulder as they danced slowly about the room. Merritt surprised himself on how well he followed; he had never danced much, except for a few times when they did it in junior high school. He had never dated a girl, either, so he had no great experience on the dance floor. Yet, he remembered in a recent visit with Beth she had taught him how a girl must follow on the dance floor, and he found he could play the role easily.

In less than three minutes, the record ended, and Billy had to release his grasp and change to another song. He picked another Hoagy Carmichael favorite, “The Nearness of You.” Soon the two were dancing again.

“That's perfect for us, Billy,” Merritt whispered into his friend's ear.

Billy drew him even more tightly as they did a slow fox trot around the room, dodging the easy chair and a coffee table they had moved to one side.

“You smell so nice,” Billy whispered back.

“Thank you, Billy. I wanted to be so perfect for you.”

“You are perfect, my perfect girl.”

They danced through half of the song, and Merritt began to feel tears in his eyes. He cursed himself for it, since he was so happy, but the realization hit him quickly. This would not last; in fact in less than an hour, Marilyn would have to vanish.

“You're so sweet, Billy,” he said. “How I'd like to be Marilyn forever.”

“I know, honey,” he said, leaning down to give him a short kiss. “Maybe you can be my prom date this year.”

“Oh, Billy, I'd love that,” he cooed.

“The prettiest girl on the floor, the prettiest girl in our class. That's you, really.”

“But I'll have to go as a boy, I guess,” Merritt said. “And that means finding a girl who'll go with me.”

“I know,” Billy said.

The afternoon continued for about an hour longer, filled with more dancing, sitting on the couch hugging and kissing. Neither boy said anything, but it was obvious to each other that they were shy about carrying their sexual pleasures further, largely because both boys were ignorant about most sexual activities and uncertain how to go about it.

Merritt's penis grew hard during most of the afternoon with Billy, but he seemed to be sobered by the reality that he would have to live his life out as a boy and then a man. He didn't begin crying until he walked home, when he feared his tears, running down his cheeks would freeze in the cold. He cried that night in bed, too.

*****
The phone rang shortly after Merritt and his mother got home on Sunday from the 11 a.m. mass, and his mother picked it up. “Marilyn,” his mother yelled, as Merritt had gone to his bedroom to change clothes. “It's for you.”

“For Marilyn?” he said back quickly. No one ever called him at home by that name.

“Yes, honey,” she said. “She said she was a friend.”

“OK,” he said, trying to use his soft feminine voice.

“Marilyn,” the voice said. He recognized it.

“Oh Dolores,” he answered, somewhat puzzled.

“I've been thinking about you since we last talked,” she said.

“Me too. I've had you on my mind. I was sorry, so sorry for fooling you.”

“I know, but I've been thinking about you so much,” she paused. “I was in such shock. I guess I wanted you so bad to be a girl.”

“I still feel I am a girl,” he said, reverting to his deeper voice. “But I guess I'm really not one. I'm weird. Why do you care about me?”

“You were so kind, so nice.”

“You too.”

“I'd like us to be friends still,” she said, suddenly.

“Me too.”

“Can we meet again, maybe for a soda or something?” she volunteered.

“Sure, I'd like that.”

“And,” she said, hesitatingly. “I'd like to see you as a boy. Is that OK.”

“I guess, but I'm not much of a boy,” he laughed outloud.

“Oh I think you'll be a handsome boy. Really.”

They agreed to go to a movie the following Friday night. Merritt hung up the phone, now feeling so happy that his honesty had paid off; he was still a friend of this marvelous, warm girl, Dolores.

*****
As pleased as Merritt felt over Dolores' renewed interest in him, he couldn't help but feel anxious over his pending date with the girl.

“Mom, how will I act with this girl?” he asked his mother one night after they cleaned up following dinner. “I don't know what a boy is supposed to do, or say.”

“Oh I think you'll do fine,” Evelyn said. “Just be yourself.”

“You mean act like a girl?”

“No silly, just be your own self. Respond to her questions, and be honest,” his mother said.

“About everything?”

“Yes, dear. From what you've told me, Dolores is a very smart girl and she's not too experienced in this dating business either.”

“I guess.”

“You said she told you she's never been on a date before, right?”

He nodded “yes.”

“Well, no doubt she's as embarrassed as you are thinking about Friday night.”

“I liked it better when we were girl friends,” he admitted.

Evelyn kissed her son, recognizing his very real concerns, and she wished totally that he would soon accept his role in life as a boy and man. She loved him both as a girl and a boy, but had to admit he made a better daughter than son. She was so pleased that Merritt was so open with her, and so eager to share his thoughts, desires and concerns. Most teen age boys, she knew, hid their lives from their parents. Not so with Merritt. Perhaps, she thought, the two had more of a mother-daughter relationship.

*****
“You're going on a date?” his friend Billy said in response to Merritt's mention of the Friday movie night.

“Yes, my first,” he admitted.

“As a boy?”

“Yes, Billy, as a boy.”

“But I love you as Marilyn,” Billy said, a twinkle in his eye.

“Me too, but I guess I better see what being a boy is all about.”

“Are you going to kiss her?” Billy said.

“I don't know,” he said, having never confessed to Billy that he and Dolores had already slept together, and done prolonged kissing and cuddling. “Besides, I don't think a boy is supposed to kiss on the first date.”

“It all depends,” Billy said.

“Are you jealous?”

“A little, but since you're not going out as Marilyn with a boy, I guess I'm not too upset,” Billy said.

Actually the two boys had developed a tight relationship, confessing to each other their darkest thoughts and most outlandish hopes. Perhaps it was their outsider status among the other students, and their general lack of confidence in being with others that created such a common bond. Billy, tall and awkward, had a pock-marked face from a childhood bout with chicken pox and short straight thick black hair along with a pointed nose. Not a handsome lad by any stretch of imagination, but with an open warm-looking face and luminescent dark eyes that one day would serve him well. But not in the doubting teen-age years.

*****
The question of what he was to wear for Friday night's date with Dolores troubled Merritt all week. He really had never concentrated much on his male clothes; he had a nice jacket and pants that he wore to church, but he felt that would be too formal for a movie date. He settled on a v-neck pullover sweater over a blue shirt and grey pants finally, looking at himself in the mirror.

He hated what he saw. The boy looking back had narrow shoulders and a thin neck, along with a rather cherubic face, that made him look puny and several years younger than his 16 years of age. He did a girly pirouette in front of the mirror, and giggled, thinking he really should go as a girl. He would have felt much more comfortable.

Yet, Dolores seemed pleased to see him when Merritt presented himself to front door at her house after the six-block walk from his home. His sorry appearance had been toughened up by the heavy winter coat he wore and the wool cap, so necessary in the cold.

“Hey you look so handsome, Merritt,” Dolores crowed upon opening the door.

“Not really,” he said, not willing to take a compliment.

“Well, you do. I didn't know what I'd see,” she said.

Dolores ushered him into the house, whispering in his ear, “Mom wants to see you now, as a boy. She remembered how pretty you were from Mrs. Buckner’s New Years Eve party.”

“Oh, really?”

“It'll be fine,” she said. “She’s OK with you. In fact, she urged me to call you up again. She thought you were nice.”

She yelled: “Mom, Merritt's here.”

Merritt's knees felt weak, and he wanted to melt away out of sight, but it was too late.

Dolores' mom was tall and thin, but also solidly built.

“Nice meeting you, Merritt,” she said, holding out a firm, calloused hand, in such contracts to Merritt’s own slender hand, soft and smooth.

“You kids are early,” Mrs. Graham said. “Come in a sit a minute.”

“So what does your father do?” Mrs. Graham asked when they were settled in the living room, after Merritt took off his rubbers.

“His father was killed in the war,” Dolores said quickly.

“My stepdad, actually,” Merritt corrected, “But I felt he was my father.”

“And he was a war hero, daddy,” she continued.

“Yes, he got the Navy Cross,” Merritt volunteered, adding that his mother worked in the hosiery mill making parachutes.

Mrs. Graham seemed pleased with these revelations, and Merritt grew more at ease as she asked some other questions, such as what he wanted to do in later life.

“I dunno,” he said. “I'm enrolled in business courses now.” It was technically true, but in reality the courses were more of a secretarial nature and mainly for girls.

“Well, you can't go wrong with that,” Mrs. Graham offered.

Thankfully, the question-and-answer process ended soon, and Merritt and Dolores were on their way.

“See, she liked you, Merritt,” Dolores said as they walked.

“I liked your mom, too.”

“I'm lucky,” she said. “You're my first real date, and I think she was more excited than I am.”

“It's my first date, too,” he said.

“We're a pair of squares, aren't we?” Dolores laughed, and Merritt giggled along with her.

Merritt felt tense the entire evening, truly not sure of whether he was acting as a boy should on a date with a girl. He had heard the other boys bragging about their “conquests” of girls, of “planking” this girl or that one, and he had always felt they were so crude. He was bothered by the tension he felt, and it certainly wasn't Dolores, who seemed to be totally receptive to his presence and seemed to like him immensely.

Yet, he wondered, how am I to be romantic with her? Will she reject my approaches, maybe laugh at me because of how awkward I was? His doubts consumed his thoughts that night, so that he hardly saw the movie they were supposed to be watching. He couldn't figure out why he was feeling so hesitant; after all this was the same girl he had found so easy to hug and kiss when he was Marilyn. Now, as Merritt, a boy, he felt totally ill at ease and inadequate.

Merritt wanted to put his arm around Dolores as they sat next to each other in the movie, but he was afraid she'd resent this move. He sat with his hands folded in his lap, trying to concentrate on the movie, “30 Seconds over Tokyo,” a World War II movie. He looked around him, seeing other couples, many with sitting with arms over the girls' shoulders, wondering whether they shouldn't do the same, but he was frankly afraid.

Finally, he felt Dolores' hand on his own, as she covered his hands lightly with her left hand, and looked into his eyes for a moment. He flushed with embarrassment for a moment, and even in the dark theater, he felt she must have felt his moment of humiliation.

Why did he feel this way? Something didn't feel right to him.

They held hands during the movie, but that was it. After stopping for a coke, they were soon walking home, and Merritt gave Dolores a short kiss on the lips at her front door.

As he walked home, he felt acute embarrassment for the entire evening. What kind of a boy must she think she was dating? I'm such a sissy, he thought to himself. I'm not much of a boy, he mused.

(To be Continued)

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Comments

I don't know how things went for folks back then...

Andrea Lena's picture

...my hope is, however, that regardless, Marilyn will get to be with whom she chooses as she also gets to be whom she chooses, no matter what that is. Love this story. Thank you!



Dio vi benedica tutti
Con grande amore e di affetto
Andrea Lena

  

To be alive is to be vulnerable. Madeleine L'Engle
Love, Andrea Lena

Another Great Chapter

RAMI

This was another great chapter in this wonderful tale. Perhaps Merritt needs Delores to guide him in what to do. But then she is as clueless as he is at the moment. Always ackward that first first date.

Rami

RAMI

I just wanted you to know

I just wanted you to know i'm still enjoying this beautiful story. thank you

Marilyn's Impossible Dream, or She's So Pretty -- Chapter 19

Back then, women would darken their legs and add the stitching on the back of the leg in pencil to make it look as if they were wearing hose. Back then, stockings were sewn up the back of the leg. It was later that seamless hosiery was invented. .

    Stanman
May Your Light Forever Shine
    Stanman
May Your Light Forever Shine

Correct History

Stanman: You're right about that. Stockings were in really short supply during World War II.

Dating

Ahhhh, a date with Dolores. Memories come flooding into my mind from my first experiences with my first date. Sadly my first date was when I was twenty. I was soooo scared! A lousy movie, a lousy date, a over all lousy night.

Funny how this story bring back such memories! Merrit and I must have a lot in common.

Vivi

Vivi