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. Can he live a double life?

(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 growing femininity has brought him into more adventures as a girl, confusing him even more as he tries to fit in at school.)

Chapter 20: The Homo Tag

Little he did in school seemed to help him come to any other conclusion that he was not much of a boy. In gym classes, he continued to be one of the weakest of boys, always losing in his weight class when wrestling and usually failing in such activities as rope climbing and doing pull-ups. He looked with some envy on other boys as they changed in the locker rooms, their arms rippling with muscles and their thighs firm with visible sinews. If he had looked further, he would have noticed many other boys didn't have such Adonis physiques; certainly some were chubby and soft and others skinny.

He was the only boy among 19 students in the Secretarial I course, in which typing skills and beginning shorthand were taught. At first the girls in the class looked at him as an oddity, and he wondered whether he should quit the course; as the semester continued, he was soon accepted as just one of the other classmates.

“You type so fast, Merritt,” Sally Orlowski said from her desk as the class was doing exercises on their ancient Underwood typewriters, the clacking raising an irregular cacophony.

“Oh?” he said, as he had finished typing the paragraph exercise just a few seconds before she had.

“I can't keep up with you,” Sally said. “Do you practice at home?”

“No, we don't have a typewriter,” he said.

“I don't know how you do it, except that you have such long fingers.”

In the typing exercises, the two of them usually finished ahead of the rest of the class, and they had developed a friendly rivalry, with Sally announcing that day as they left class together: “You beat me today, and that means you're ahead of me now. You've won three times, and me only twice.”

“Oh I'm sorry,” he said, and he truly was sorry, since he and Sally had developed a warm friendship and he didn't want to hurt her feelings.

“No, no, Merritt, I'm not sad,” she said. “I like competing with you. It's fun. I'll beat you tomorrow.”

He smiled.

“But how do you do it?” she asked. “You're a boy and now you're better at typing than all the girls.”

Merritt didn't know how to answer her; he wanted to tell her the truth that the deftness of his fingers probably came to the fact of his sewing, a talent he was trying to hide, for fear of the teasing it might prompt from other students, particularly other boys.

Several times Sally joined him at the lunch table. He enjoyed the fact that the girl did this on her own accord, rather than sitting with a gaggle of girls who were from working class families and seemed to separate themselves from the girls from the Highlands, an affluent part of the community. The girls from the flats -- a low area along the River -- tended to be taking non-academic courses, like Secretarial and Dressmaking and were mainly interested in finding a husband before their 20th birthdays.

Sally was slender, fairly swarthy in complexion, likely due to her Polish heritage, with tiny breasts. Her hair was dark and fell loosely about her shoulders, and Merritt thought she was beautiful, even though her dresses were often shapeless and plain. Her beauty, he felt, must come from her always cheerful and upbeat attitude, always ready to find humor in some of the mundane happenings in school.

“Tommy is getting jealous,” she announced on that lunch period. “I'm always talking about you.”

“Oh?” he asked, wondering what she was saying.

“I just tell him how nice you are, and how you've helped me in class, but you know how boys are. He wants me all to himself.”

“Yes, I guess I do,” he said. “I do like you, Sally, but I wouldn't want you to get in trouble with Tommy.”

Tommy was a burly lad who was an ordinary to indifferent junior who had constantly oil-stained hands from his parttime job at Joe McBride's garage. Chances are he'd volunteer for the Army right upon graduation, and probably looked to take Sally as his bride in the process. The idea haunted Merritt, not that he had any romantic designs upon the girl, but that he felt Sally was a talented lovely girl who deserved better than a life as a harried mother with four or five dirty-faced children living in the flats.

“I know you don't Merritt,” she said, leaning over and beginning to talk in a whisper.

“Can I tell you something, Merritt?” her voice was hesitant.

“Sure.”

Their voices were low now, and the cafeteria table was empty except for the two of them.

“I don't want to hurt your feelings, Merritt,” she began, “But, I almost look upon you as a . . . how should I say it? . . .”

Merritt suddenly had the feeling he knew where she was headed with the conversation. Nonetheless, he urged her to continue. “As I what? Go ahead, I won't mind.”

“As like I would another girl friend,” she whispered so softly now he barely heard the words.

He was momentarily dumbfounded and didn't know how to answer, realizing how true he remarks actually were. How could he feel any differently?

“Oh Merritt, I'm sorry, but it's true.”

“That's OK,” he admitted. “Sometimes I feel like that too, that I'm like one of the girls. I feel I'm just different.”

“Different, but nicer.”

He smiled, adding: “But I'll still beat you tomorrow in typing.”

“No you won't,” she giggled.

*****
Two days a week, on Wednesdays and Fridays, the class took shorthand, using the Gregg system; it meant complicated drills and repetitions of symbols, employing the squiggles and little tails of lines that so featured the popular shorthand of the era.

“Girls who know shorthand will almost always get a job,” Miss Appleton, the Secretarial Class teacher, told them.

Suddenly she spied Merritt in the classroom, adding that boys will always find the skill useful if they go to college for note-taking or even as courtroom reporters. The tallish, severe-looking woman, her hair tied back in a bun was still uncomfortable having a boy in her class, since she kept referring to her students as “girls.”

“Now for your posture, young ladies,” Miss Appleton began during a Friday class period, this time forgetting to correct herself to include Merritt in the references.

One of the girls, Amy O’Hara, sneaked a look in Merritt’s direction, when Miss Appleton referred to “young ladies” and smiled conspiratorially. Merritt blushed and looked away.

“Sit erect, ladies,” the teacher continued. “And hold the pad in your hand, meaning your left hand if you’re right-handed and right hand if you’re left-handed. Some of you girls may find it easier to cross your legs, but you must cross your legs very daintily, like this.” She demonstrated, carefully pulling her skirt down so that her knees were not exposed.

“Never, ever, girls, wear a skirt that is so short that the person who is dictating can see above your knees as you sit,” she said, still ignoring Merritt.

Out of the corner of his eye, Merritt could see Amy was trying to suppress a giggle, while looking in his direction. He wanted to hit the girl for her obvious enjoyment at this ridiculous situation.

“Now, all of you, I want you to stand up and sit down as I told you, folding your skirt underneath you as you sit,” the teacher continued.

Merritt joined the girls in the exercise, even pretending he wore a skirt as he sat down. He felt he had participated perfectly.

“Good,” said Miss Appleton. “Most of your girls did just fine, but Amy O’Hara you don’t seem to be taking this seriously. You sat down almost like a boy and your posture was terrible.”

“I’m sorry, Miss Appleton,” Amy replied, still trying to stifle a laugh.

“What’s so funny, girl?” the teacher demanded.

“Nothing.”

“It’s not nothing, Amy O’Hara. Are you laughing at the teacher?”

“No, Miss Appleton.”

“What, then? Out with it girl. Share it with the class.”

“I can’t,” said Amy, a round-faced, chubby girl with freckles.

“Well?” The teacher stood over Amy, staring down at her, bringing the girl nearly to tears.

“Oh,” Amy said finally. “It’s just that you keep calling us girls, and there’s a boy in this class.”

Miss Appleton looked shocked, finally saying. “Of course there is and he’s one of the best students here. I don’t see anything funny in that. He executed the proper position perfectly. You should follow his example, Amy.”

Merritt suddenly felt so exposed to the girls in the classroom. He knew his years of pretending he was a girl had resulted in picking up feminine habits and mannerisms. Maybe Miss Appleton saw that femininity in his presence in the classroom and unthinkingly considered him to be one of the girls.

“Now, enough of this,” she said finally, changing the subject. “I’ll dictate a few simple sentences. If you studied your Gregg assignment, you should all know them.”

As the teacher began to dictate, Merritt assumed the proper position automatically and he could see Amy eyeing him warily as he began his shorthand scribbles. Suddenly he felt curiously dividing, feeling both humiliated and elated at being identified as assuming his posture in such a feminine manner.

*****
“Tommy’s not jealous anymore,” Sally said to him when they were seated together at lunch.

“Oh, how do you know?” he responded. The two were talking in their conspiratorial whisper.

“He thinks you’re a homo, and so he doesn’t care if we’re friends.”

“A homo?”

“Yes, although I don’t think so,” she said. “I just think you’re nice.”

“Thank you,” he nodded.

“A lot of guys think you’re a homo,” she added. “But just because you are always neat and are so polite doesn’t mean anything.”

“I just like being neat,” he said. “And I like being with girls a lot, I guess.”

“I must say that in shorthand class today, you really did act like a girl when you sat down, a lot better than Amy. She shouldn’t have laughed.”

“I was just doing what Miss Appleton wanted us to do.”

Sally put a hand on his slender forearm, looking at him. “I think you’re one of my best friends, Merritt, even if I sometimes think of you as a girl.”

Just then the bell rang, alerting them to class. Merritt was disturbed by this conversation, and it clouded his mind as he went through the afternoon classes.

*****
“I have a girl friend, Sally,” Merritt explained after school, as he joined her for the walk home. They both lived in the same general direction.

Merritt had caught up with the girl, who was cradling her book in her arms at her breasts. He was eager to tell her that he wasn’t a homo, or queer, or a fairy, the popular terms of the day, all derisive.

“I didn’t say you were a homo,” she said quickly. “That’s just what Tommy says you must be, taking typing and shorthand and all that.”

“I didn’t think you thought that,” he said. “You’re such a nice friend.”

“You too,” she said. “Where are you headed now?”

“Home, and then to my job.”

At that moment, Sally slipped on an icy spot in the walk. She righted herself, with Merritt grabbing her arm, and both of their books and looseleaf binders fell to the snowy boundaries of the walk, papers blowing in the wind. The two scrambled to gather them up, finally managing to do so.

“Oh, I didn’t see that ice,” Sally said. “Thank you, Merritt.”

She quickly gave him a quick kiss on the cheek, apparently in gratitude for his quick action in keeping her from falling.

“You’re blushing,” she said, as she drew away. “That’s so cute.”

“It’s just the cold,” he said, defensively.

“No, you’re blushing, Merritt. Don’t lie to me. Haven’t you ever been kissed by a girl before?”

“Yes, I have,” he protested.

“I love it when a boy blushes,” she said. “How many girls have you kissed?”

Merritt hesitated, finally answering, thinking of his awkward date with Dolores and of his “girl time” with her: “Just one, I guess.”

“You’re cute,” she repeated.

Hoping to change the subject, he asked her: “Do you work now?”

“Yes, I work some after school and Saturday at the five and dime store,” she said.

“Which one?”

“The Ben Franklin. And where’s your job?”

“I help out at Swenson’s.”

“Oh, the fabrics store and the dressmakers?”

“Yes, we live upstairs over the store. It’s handy.”

They were near 2nd Street, where they’d break apart and Sally would go north and he south to their respective homes.

“What do you do there, Merritt?” she asked suddenly.

“Just help out,” he said, hoping the questioning would end soon.

“Really?” she queried. “I’m told they do lots of nice dresses there, even prom dresses.”

“Yes, they do,” he agreed.

In fact, the store was slowly getting a reputation for its great, and relatively inexpensive, dress designs. Mostly it was said that the Swensons had a great seamstress.

“Who’s the seamstress there?” she asked.

“Oh,” he said, his face growing red. “My mother,” he lied, knowing he had been doing most of the sewing since her mother’s job in the hosiery works included so much overtime.

They stopped the corner, and Sally, held him from leaving.

“Ever help her out sewing, Merritt?”

“A little,” he finally admitted.

“I thought so,” she said, triumphantly. “That’s why your fingers move across the typewriter keys so easily.”

He nodded, trying to turn away and leave.

“I bet you do lots of sewing, don’t you?” she pressed. “You are always so neatly dressed. I’ve never seen a boy so clean and neat as you.”

“Oh I just like being neat,” he said.

“Well, I like you, Merritt, and I bet you’re good at sewing, too.”

“Pretty good,” he agreed, reluctantly. “But I don’t like to tell people that. Most don’t think a boy should be sewing.”

“I guess not, but you’re secret’s safe with me, Merritt,” she said, turning to leave.

“Yes, please don’t tell anyone, I get called enough names as it is,” he said.

“I know, and I won’t. You’re sweet boy.”

He walked home disturbed how easily his secret came out. He knew he’d have to get another job if he was ever going to be accepted as a boy.

*****
Later that afternoon, as the day darkened in the early dusk of winter, Merritt lost himself in fashioning a new party dress for Abigail Hunter, a 16 year old girl from one of Riverdale’s affluent families. The girl was quite chubby, but insisted on having a dress that exposed her shoulders and arms, as well as her husky thighs.

“I tried to talk her out of such a dress,” Hilda Swenson told Merritt, as he settled down with patterns the girl had chosen while stopping in the shop. “She shouldn’t show that much skin, I told her, but that’s what the girls are wearing this year.”

“She should at least wear a wrap with it,” Merritt agreed, looking at the measurements Hilda had taken. Judging from the measurements, Merritt felt he would be designing a dress for a pig, but he wouldn’t say that out loud.

“Maybe you could fashion one for her, and we can just add it to the dress without charge,” Hilda said. “You know this is the first customer from the Highlands area, and maybe if we do this one well, we’ll get more business.”

Merritt was aware that the dress-making side of Swenson’s Shop was getting more and more business; among the families in the “flats,” the word was out that Swenson-designed dresses were not only affordable for the low-incomes of the flats families, but were stylish as well. Merritt was largely responsible for the success of their custom-made dresses, he knew, but was more than happy to let Hilda and his mother take the credit.

Making Abigail happy would be a challenge, Merritt knew, and that helped to take his mind off his troubled discussions with Sally on the way home from school. He got lost in his work, finally picking a dark violet material that he felt would help create a classy dress, and give him some hope of making his client look slim and attractive. It would be difficult, but a happy result would bring new fans to Swenson’s and more earnings for both the Swenson’s and himself.

Before he started on Abigail’s dress, Merritt completed putting finishing touches on a dress for another customer, one of the neighborhood girls who was in her freshman year of college and needed a dress for a sorority dance. The girl had a trim figure, judging from the measurements, and Merritt had not liked the belt he had designed to cinch her waist tight, and he had created a new cloth belt. As he often did, he closed the door to his workroom, locking it, and climbed into the dress himself. He did this on a regular basis, as he explained to a curious Hilda Swenson, to see how a dress would hang.

“Can’t you tell from using the mannequin?” Hilda asked him one day.

“Not really, it doesn’t show the natural curves,” he replied, embarrassed by her question, since he felt she must have suspected his real reason was that he liked to wear dresses.

Merritt was particularly fond of this dress, as he was aware that the customer had nearly the same dimensions as he did, except in the chest area. He took particular interest in creating a lovely dress, one that he himself would be proud to wear. When he modeled dresses, he put on bras and stuffed them to match the girl’s own measurements.

Once dressed, he examined the finished product in the full-length mirror, always astonished at how completely feminine he looked. Usually, he asked either his mother or Hilda to judge the dress, too.

“What a lovely girl I see,” he said softly to himself. He smiled, taking a few movements that would have wowed judges on a fashion runway.

He added a necklace and a pair of clip-on earrings, along with a pair of short heeled-sandals he kept in the shop to create a full package of femininity. Unlocking the door to the workshop, he called to Hilda to examine the final product.

“That is a masterpiece, Merritt,” the shop owner said. “And you look particularly ravishing in it, dear.”

Merritt twirled about, having the full skirt flow in the wind, as he viewed his slender, shapely legs and pretty shoulders which accentuated the dress. He particularly liked the shoulder treatment of the dress. It had been fussy work, creating and sewing ruffled shoulder straps that formed short sleeves and created a square bodice.

“Sit down, Merritt,” Hilda said after he had shown the dress from all possible angles.

“I have been wondering about something,” she began. “You’ve been the key to our success this year in the business. We’ve never had so many dress customers and more and more are coming, just by word of mouth. They like what you’ve created.”

“Thank you, Mrs. Swenson,” he said. He was seated primly, his legs crossed and his slender hands folded on his thighs.

“Maury and I were talking, and we think we should reward you in some way, such as making you and your mother partners in the store. We’d like also to begin advertising the dressmaking we do — actually, you do — to a wider sets of clients, and maybe even letting you create a line of clothes.”

“I don’t know, Mrs. Swenson. What would mother think?”

“I’ve sounded her out on the idea, and she wants me to leave it up to you, dear.”

“I don’t know,” he said. “It sounds OK, but I still don’t know.”

“That’s OK, you have time to think about it,” she said. “By the way, would you like to make a copy of this dress?”

“Yes, I would,” he said enthusiastically.

“It’ll be yours, honey, but we may want to use it as a model to promote the business,” she explained. “The store will provide the material for you.”

He smiled. He loved the dress, and gave Mrs. Swenson a quick kiss.

*****
“Oh mother,” he said excitedly to Evelyn that night. “I just finished my favorite dress of all time, the prettiest, loveliest dress ever.”

“I know, Hilda told me about it.”

“And, I’m going to make a copy for myself. I look so beautiful in it, mother, really . . . so beautiful.”

“Honey, calm down,” Evelyn said. “Did she tell you what else she has in mind?”

It was a night for Marilyn, and he was dressed in a plaid skirt, white blouse, and pearls and wore saddle shoes with short white socks, making him look like a cute school girl. He sat down on a dining room chair, his knees together, hands folded primly.

“Yes, she did,” Merritt said, his giddy joyfulness suddenly subdued. “And I don’t know whether we should do it.”

Evelyn drew her chair close to his, taking his hands in hers, feeling the warmth exuding from the boy’s dainty hands.

“I think I understand,” she said. “You have such a great talent, though, Merritt, and this might be an opportunity for your future.”

“I know mother, but I would really be heading my life into one of dresses and fashions and being so totally feminine, and I’m not sure about that.”

“It’s a choice, and sometimes,” Evelyn said, “It seems that’s what you are and want to be, a girl and a woman.”

“I know, mother,” he said, “And it would be so much easier if I could turn into a woman right here and now, but that’s not possible. God made me a boy.”

Tears began to form in his eyes, and his mother lightly patted his hands, letting the moment linger.

“What do you want to do, honey?” she said. “You’re taking secretarial classes now and you’re good at that, but you could be so successful as a dressmaker. And make so much more money.”

“I don’t even know if I wanna be a secretary,” he said. “That’s no job for a boy . . . er . . . for a man.”

“Well, we don’t need to decide now, honey, but Hilda was sweet to make the offer.”

She kissed her son, his perfumed scent permeating the air. He was so pretty, so totally girlish.

*****
Merritt became more and more aware of the progress of the War as the winter of 1944-45 progressed. After the promise of the Allies taking Normandy in June 1944 had soured, due to the ambush worked by the Germans in the Battle of the Bulge, causing great casualties to U.S. troops, Merritt became conscience of the terrible horrors of war.

For a history course required essay, he dug into newspaper files to study the landing at Tarawa that had claimed the life of his stepfather, realizing the terrible loss of life in that ill-planned attack. He heard of the terrible bombing of Dresden by U. S. planes which had killed many civilians; even though they were citizens of the enemy country, Merritt felt it was unfair.

At first, Merritt kept his thoughts to himself, thinking he may be bordering on being unpatriotic. After all, shouldn’t he believe in the United States and its greatness. Well, yes, he did, but it still seemed that war had terrible horrors. Was there not a way to end such wars?

The cold winter was nearing an end, and as they walked home one day, he hinted about his concerns to Sally, fully expecting a rebuke from her.

“It’s awful, isn’t it, this war business?” she replied.

“But the Nazis are evil and the Japs, too,” he responded.

“Oh yes, we had to fight this war, but this should be the last war in history,” she said. “No more wars after this.”

“That would be great,” he said. “I guess there’s talk about having something like the old League of Nations.”

“It’s got to be better than that,” Sally said, surprising Merritt with her knowledge of world affairs.

“I know, the League had no power and the U.S. didn’t even join.”

Merritt’s interest in the war and its causes prompted him to read every issue of Time Magazine that the Swenson’s got, covering the news sections thoroughly. He shared his and Sally’s discussion with Billy Johnson, who also had been gaining greater interest in current affairs.

“I’ve heard of something called the World Federalists,” Billy said a few weekends later, as the two were listening to records at the McGraw flat. “It would be like a United States of the World, and could take away the need for wars.”

The idea intrigued Merritt, and soon the three of them were discussing forming some sort of a group at Riverdale West; it turned out, as well, Edith said she was with a group of girls at Our Lady of the Angels Academy were talking about the same idea. It appears that a national organization, called the United World Federalists, was leading the effort and was organizing student chapters across the United States.

The idea had become so consuming to Merritt that he forgot to tell Billy of his new dress, the copy had had made. He wanted to wear it and see what his friend thought about it.