(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. Now in his sophomore high school year, Merritt finds his effort to become more and more masculine challenged. )
Chapter 22: Into a Boy’s Life

Merritt was acolyte for the Holy Week services at St. Patrick’s; that meant he’d wear vestments that almost matched those of the priest. He’d be serving and preparing the altar for the Holy Thursday services, the three-hour Good Friday marathon and the dawn mass on Easter Sunday. While many of his friends enjoyed the full week of vacation, Merritt’s week was busy in the shop, where the dress-making business had gotten demanding as the prom season was nearing. Teen girls in the area had learned of the bargains and fashionable dresses that came from Swenson’s, and were flocking into the shop in such numbers, that Hilda Swenson finally quit taking measurements and orders. Thus, Merritt’s hope to escape the dressmaking business to work in more typical male work had to be postponed. Merritt was stuck with making most of the dresses, but his mother would plan to work evenings to help out, after her day job on the hosiery works ended.

In truth, he hadn’t been completely true to his promise to refrain from wearing girl’s outfits during Lent. After trying for a few nights to sleep in boy’s pajamas, he gave up. They were too scratchy, he told his mother, returning to the smooth satin of his nighties; he particularly loved the frilly ones that came down almost to his ankles. Now, his only “girl time” was at night, when he prepared to go to bed.

“The ladies of the Altar Society love working with you, Merritt,” Father Mulcahy told the boy as he arrived for the Good Friday services. “And I’m so happy having you here, too.”

“Thank you, father. I’m enjoying it too. Those ladies are fun to work with,” he said, smiling.

“I just wanted you to know that. They told me you’re the most attentive acolyte they’ve ever had and they like that.”

It was true, Merritt realized, that he so looked forward to helping to decorate the altar for the Easter time in order to celebrate the Lord’s rising from his tomb in joyous celebration. He found great pleasure in using his designing skills, perhaps gained through his dress-making, to prettify the church. There were about a dozen ladies, nearly all grandmothers, in the society, and usually about half of them showed up at a time to work on the altar.

One woman, Mrs. McGonigle, brought along her 15-year-old granddaughter, Eileen, to assist in the Saturday preparations. She was a shy, slender plain-looking girl with straight shoulder-length brown hair who stood around awaiting instructions as to how to help. Merritt eyed her as he stood on the ladder, attempting to attach a garland to a wall; seeing her standing helplessly, he motioned her with a nod of his head, to come over and hold one end of the garland.

“Thank you, Eileen,” he said once the chore was completed, and he had descended the ladder.

The decorating continued for another hour, and when it was finished Mrs. McGonigle and Eileen left without further words with Merritt. He was disappointed; something with Eileen intrigued him, but he couldn’t figure out why. She was shy and nondescript and had a body virtually without shape; for some reason he pictured her growing up and living out her life as a spinster librarian. He should have pitied her, he felt, but he found himself wishing he could trade places with her.

He hoped he’d see her again soon. He never did, and when he boldly asked Mrs. McGonigle about Eileen, she replied tartly: “She’s gone back to mother in California. She’ll not be back.”

Merritt wanted to inquire further about the girl, but Mrs. McGonigle’s short, almost rude answer made him stay silent. For some reason, the image of Eileen would remain with him the rest of his life, popping up at the strangest times.

When the ladies of the Altar Society finished their work, they stayed around to enjoy tea and cookies together, one of them usually having brought treats each session. Merritt joined with them, finding he loved the conversation, so often about the fortunes — or, more usually it seemed, misfortunes — of their children or grandchildren.

“We’re so happy to have you join us, Merritt,” one of the ladies said. “But aren’t you bored with us?”

“Not really,” he said. “I like the cookies.”

“Oh you can take your cookies and go, if you wish,” she replied. “I can’t imagine a boy would enjoy sitting with us old biddies.”

Merritt blushed, not knowing how to respond. “You’re all nice,” he said, finally.

“Thank you and you’re so sweet, too,” she said, patting his knee.

Merritt noticed he was holding his tea-cup in a lady-like manner, just like the others; and, his legs were crossed, also very lady-like. It seemed he just fit in perfectly.

*****
“Come on, Marilyn,” his friend Billy Johnson pleaded. “I want to take you out on a date, just like you were my girl friend.”

“I can’t, Billy,” he said. “Really, I promised mom and I said I’d try to be more of a boy.”

“You’re prettier than any girl I know, and certainly no real girl as pretty would go out with me.”

Billy was probably correct about that; his slender body, a gaunt face and scruffy dark hair hardly gave him an appealing look, and the boy knew it. His saving grace was his ready wit, his generous eyes and generally nice demeanor. In fact, both boys had often discussed how difficult it would be for them to get dates, and possibly ever find a girl who’d marry them. They were linked by their common feelings that they were unattractive to women.

“I can’t,” Merritt repeated.

“Well, anyway, you can at least dress up for me at your place some day,” he persisted. “OK?”

“OK,” Merritt agreed. And he knew just exactly the dress he’d wear; it was one he had created for Dolores, and which he planned to give her as a gift. He had tried it on several times, and with some filling for the chest, it fit perfectly. And, he knew, he looked divine in it.

*****
Merritt’s mother was planning to go to a union meeting Wednesday night, and he invited Billy Johnson to join him then at the family’s apartment. It was Merritt’s routine to work several hours after school at Swenson’s, finishing in the workroom about 6 p.m.

“Come over about 7:30. Mom’ll be gone and I’ll be all pretty for you,” Merritt whispered into Billy’s ear during lunch hour on Tuesday. He spoke in soft, inflected tones, perfectly mimicking a sexy young woman.

They were seated together on a cafeteria table, and Merritt sensed his friend tense up, gaining almost immediate sensual stimulus from the expectations of being with him as “Marilyn.”

“I still think you should go out on a date with me,” Billy whispered back.

The prospect also excited Merritt as he pictured himself, slender and lovely on the arm of a tall young man. He had tried on the dress he was making for Dolores, and after doing a few touch-ups that night, it would be ready for him to model for his friend. While Merritt told himself he was making the dress for Dolores, the truth was most of the time he was seeing the image of himself in the dress. He was really making the dress for himself, wasn’t he? Yes, but Dolores would have the finished product, and he felt that justified his own selfishness.

Merritt had chosen to make a gown of light blue taffeta, with an Elizabethan collar, full sleeves, belted with skirt flowing to the ankles. He incorporated a bit of fussiness along the trim, giving the gown an elegance that was rare among prom gowns. He wondered whether he had gone a bit over the top in the design, but he felt the need to hide Dolores’ husky, strong arms and give her a stately presence. She had seen some photographs of a similar design and had expressed a desire for such a dress.

In truth, the gown was a slightly bit too big for him; in the fitting for Dolores he found her frame to actually be a bit broader than his own more dainty body.

“You’re so elegant, Marilyn,” Billy said upon arrival.

“Thank you, sir,” Merritt said, curtseying before his friend.

“You look like a queen, Marilyn,” the boy said. “Almost too regal to kiss.”

“Try it anyway,” Merritt smiled.

And Billy kissed him tentatively on the lips, as the two hugged gingerly, careful not to muss the dress.

Merritt had put a stack of records on the phonograph machine, ready to play 10 songs on the 78 rpm discs of sweet sentimental dance tunes, mainly from Glenn Miller, Tommy Dorsey and Artie Shaw. He even had two songs with Frank Sinatra, singing with Tommy Dorsey’s band. He switched on the phonograph player, and welcomed Billy to lead him out to dance in the tiny living room of the apartment.

“You’re so romantic,” Merritt cooed as they danced.

“I have the prettiest girl in the room,” said the other.

“The only girl.”

The two laughed.

Yes, for a too brief hour, he was Marilyn, a lovely, sweet, shy girl in the arms of her man. It was heaven.

*****
“Do you still like me?”

The question came out of the blue as Merritt and Dolores stood outside her house. It was a warmish April evening, after a teaser of an almost summer-like day which almost always in this northern climate was followed by chills and nastiness. But the two young people had enjoyed the evening seeing a movie at the Tivoli, stopping at Morgan’s for a soda and walking home. He had not so much as tried to put his arm around Dolores in the movie, or even hold her hand.

“Of course, I do,” he said. “Why do you ask?”

“I don’t know, you just seem so quiet tonight.”

“I suppose.”

He knew he had acted distant to the girl this evening; he himself couldn’t explain it, since he was distinctly fond of Dolores and wanted her always to be his friend. Maybe it was because he still was trying to get used to the idea that she wanted him as her “boy friend,” not as just a friend, so much like a girl friend. Was he uncomfortable trying to be a “boy friend?” What was he to do? Some boys seemed quick to force their affections on a girl, to demand a hug or a kiss and then to feel them up and do all those nasty things boys do to a girl. That wasn’t him. He liked being with her as a“girl friendj.” That seemed natural to him.

“Can I ask you something, Merritt?”

“Sure.”

“I hate to ask this,” she began. “I love the dress you gave me. It’ll make me the classiest girl in the room.”

“Thank you, I loved making it.”

“Well, Jimmy, my cousin, who was going to take me to the Angel’s prom can’t now. He’s got measles and will be quarantined until after the prom.”

“That’s too bad.”

“And I don’t know anyone else to take me. Can you be my date? It’d be a shame to have this dress not used.”

Merritt truly wasn’t pleased with the idea. It would mean he’d have to act like all the other boys at the dance and he wasn’t sure how he’d do. But Dolores was such a friend.

“Really, no one else?”

“Well at an all-girls school like Angels, you don’t see boys in your English class,” she said, nervously. “And we’d have fun, Merritt. Please.”

It was not unusual for girls at Our Lady of the Angels to ask boys to dances at the school; often times they had set up dances and brought in boys from Don Bosco High (an all boys’ school) for mixers.

He agreed, and recognized Dolores would help him through the night; she’d never embarrass him and, she was right, they might have fun.

*****
Merritt faced his prom date with Dolores with apprehension. He hoped dearly that he would be a credible boy once he was dressed in his black tuxedo, rented for $10 — a truly large hunk of money for the cash-strapped McGraw family. He had always shied from traditional “boy” roles, and this, outside of the movie night, would be his first real date with a girl, and he hoped Dolores would be proud to be on his arm for the Grand March and the other activities of the night.

Evelyn fussed over her son as he prepared for the date, and had insisted he have his hair cut for the dance. The trip to the barber was, in itself, worrisome enough, since Merritt had had his hair traditionally cared for in the beauty salon located next to Swenson’s craft shop. Betty Harrison, the salon proprietor had been a wise caretaker of the boy’s hair, following Evelyn’s orders to keep it longer than usual, but still fashioned in a boyish style.

The boy went to the shop on his own, and waited patiently for 20 minutes before his turn came up, viewing old copies of Field & Stream and The Sporting News. He was shocked at the photos of men holding long guns and posing with dead deer and elk strung up in firing line fashion. He found the baseball statistics that filled The Sporting News of more interest, since he had developed an interest in the minor league Riverdale Pirates that performed in town, thanks to the influence of Uncle Frank. Since moving in with Merritt and his mother, Uncle Frank had nurtured the boy in the ways of men, but had done so gently and with patience for the boy’s ignorance about many such topics. Merritt mused deeply about his uncle, who had proven to be a gentle man, in spite of being severely injured in the war; he still carried a spattering of shrapnel in his leg and buttocks from the German grenade that exploded near his foxhole during the Battle of the Bulge.

He was deep in thought when he heard his name called by the barber, who had to repeat it twice before Merritt responded.

“Guess we’ll have to clear that long hair from your ears, young man,” the barber said loudly, to the chuckles of the men in the crowded shop.

Merritt rose to go to the chair, his face red with shame. He wanted to run from the shop and never return, but the barber had a surprisingly warm face surrounded by a full head of grey hair and sparkling blue eyes. He looked friendly and welcoming as he held up the barber’s apron, ready to cover Merritt with it once he was in the chair.

“Come child,” the barber said. “Just teasing you a bit, boy. You’ll have to get used to it.”

“Yes, sir,” Merritt said, still humiliated by the remark. He settled in the chair, and welcomed the apron as it was placed over his body.

“You have beautiful hair,” Ernie, the barber, told Merritt on his trip to the shop on the Saturday before the prom. “I’d like to trim it a bit, but not cut it too closely. Is that OK, young man?”

Merritt smiled, and nodded.

And the barber did, indeed, put Merritt at ease quickly, asking him if he liked any sports. Merritt said that he did.

“I like the Pirates and I’m on the tennis team at West,” he said. Both were true, but the information he knew didn’t reflect the real Merritt. These two interests were secondary to his desire to be a pretty girl.

“Oh, I played tennis too, when I was younger,” the barber said. “It’s a tougher sport than many guys think.”

“Yes, you’ve got to be quick on your feet,” Merritt agreed.

The day in the chair ended positively, with the barber both trimming and thinning the boy’s long hair to a more masculine style; yet, Merritt felt, it would still be long enough to curl and make long more girlish, if he wished.

“Come back again, Merritt,” the barber said, as he gave over a quarter for the cut, plus a dime tip, as his mother suggested.

As he left, he thought he overheard the barber say to another barber, “First time he’s been here. Seems like a nice young man.”

Merritt felt good; it was the first time he recalled leaving a bastion of masculinity with some feeling of acceptance.

*****
Several days before the prom, Dolores called to say that she suggested to Donna Mae, Merritt’s longtime friend and a fellow student of hers at Angels, that they double-date. Donna Mae was being escorted by her boy friend, a jock named Richard Mason.

“Is that OK with you, Merritt?” Dolores asked. “He’s got his license and he can drive the family car.”

“I guess,” Merritt said. “I thought Donna Mae would be doubling with Edith.”

“I think Edith doesn’t have a date.”

“No date? What happened with John?” Merritt asked, referring to Edith’s boy friend.

“They broke up last week.”

Merritt felt crushed that his friend had no date. He thought that Edith really liked John, although Merritt could not understand why: the boy had a great love for himself and was quite a braggart, but he was handsome and tall and considered a “catch.”

The night of the prom Merritt agreed that Richard would pick him up at Donna Mae’s and then they’d pick up Dolores and head to the high school gym for the dance. Merritt bought a corsage for his date at Mary’s Floral Shoppe for $6, leaving him about $10 left for whatever refreshments they’d buy at the dance and for a dinner afterwards.

Dolores was ravishing in her dress, just as Merritt hoped she’d looked. The group had to spend time at Dolores’ home, while her father took pictures of the couple, both looking resplendent in their outfits. He even took a shot of all four teens.

“What a handsome group!” Dolores’ mother gushed.

Merritt was concerned about doubling with Donna Mae and Richard, since he knew Richard to be such a masculine young man and a popular athlete. By comparison, Merritt felt so inadequate and unequal; what would they say?

Richard, however, turned out to be friendly and open to conversation. He treated Merritt as an equal, perhaps because he must have known that Donna Mae may have told him to. Donna Mae could be very persuasive, he knew.

“I’m such a klutz,” Dolores said, as the two began dancing to “All of Me,” their feet colliding a couple of times.

“No it’s me,” Merritt said.

“No honey, it’s not you. You’re a good dancer. Really.”

“You can thank my mom for that,” he said. “She taught me how to dance. And we practiced this week.”

“I wish someone had practiced with me.”

All had gone well until they began dancing to “Begin the Beguine,” which the band was playing as a tango; most of the couples on the floor were struggling to get the beat right, some evening trying to jitterbug to it with awkward results. In the midst of the dance, Merritt and Dolores collided with another couple, a tall beefy red faced boy and his chubby blonde partner.

“Watch where you’re going, fairy!” The boy said addressing it to Merritt.

Merritt was shocked and tried to steer Dolores away from the couple, but Dolores resisted, turning instead to the boy, saying, “Watch out yourself, fat ass.”

“What?” the boy said, stopping his dancing in the middle of the floor.

“Fat ass,” Dolores repeated, as Merritt tried to move away.

“If you weren’t a girl, I’d punch you,” the boy said, as his girl friend protested, trying to move the pair away.

“Try it and I’ll wipe you out,” Dolores said, and Merritt knew that she meant it, and might even prevail over the boy. “Don’t ever call my friend a ‘fairy.’ He’s twice the man you are!”

Merritt finally succeeded in separating the two couples, just in time to see a chaperone warily eyeing the confrontation.

“Thanks,” he whispered. “I could never have done that.”

“I know,” she said. “And I love you for it.”

“You defended me, and I should have defended myself. I don’t think I could have,” he admitted, as he drew her closer and their dancing seemed to grow more and more in sync.

Yet, the “fairy” word bothered Merritt; did he look so much a sissy, even in the tuxedo, that a strange boy would mistake him for a homosexual? And, what did Dolores mean by remarking the he would be “twice the man” to the boy she called a “fat ass.”

*****
Prom night, of course, doesn’t end when the dance does. It’s mandatory that the couples do something. In the 1940s, however, resources were tight, and there were no motel rooms booked or beery post-prom parties; some boys however felt it was timely to “get in the pants” of their dates. Others, who were more timid, shy or just more restrained chose to go to a nice restaurant for a late night meal, with the hope for some “necking” in the car before they drop their date off.

Merritt was uneasy with the prospect; he just wasn’t comfortable trying to hug and kiss Dolores. He knew it was strange, since he had already slept with her when he was Marilyn. He was comfortable when she thought he was a girl, and they could, as two girls, kiss and hug passionately. Of course, there was no more explicit sex between the two. But, now, on prom night, he was expected to be a boy. Could he do it?

Like several other groups of West High prom-goers, the four chose Toy’s Chinese Palace, a popular restaurant downtown on the second floor over the Walgreen’s store.

Charlie Toy, the aging proprietor, greeted all of the prom groups in person, leading them with great aplomb to their neighbors, and in his broken English saying “Here you are, kings and queens.” He called them all “kings” and “queens,” maybe because his own children had gone to West High, and he was so proud to serve others from the school.

“What happened with you and Wayne?” Donna Mae said, addressing Dolores.

“Wayne?”

“Yes, that boy you and Merritt bumped into on the dance floor.”

“Oh that, he tried to wise-off,” Dolores said, smiling. “I called him a fat-ass.”

“Good for you,” Richard said. “He’s a bully, but I think any of us could beat him up, if we had to.”

Merritt was startled; he never considered ever being in a fight with anyone. Dolores must have known what he was thinking, since she leaned over to him and said, “Even you, Merritt.”

It was an awkward moment, and Richard seemed to sense that, for he quickly changed the subject, saying, “I understand you’re on the tennis team, Merritt.”

“Yes, I’m playing No. 3 singles,” he said.

“He’s won three of his matches so far,” Dolores said.

“Good for you,” Richard said. “Maybe we can all play some time. You and Dolores against me and Donna Mae.”

“You don’t play tennis, Richard,” Donna Mae said.

“I know, but you can teach me,” he smiled.

Richard was an end on the football team and during the spring played third base on the baseball team; he had the ruddy complexion of a muscular athlete, his veined hard arms in contrast to Merritt’s slender arms, smooth and without muscular definition.

“Let’s hope this war ends soon,” Donna Mae said. “My brother’s over in France, and we haven’t seen him in two years.”

“I think it might,” Dolores said. “The Allies and the Russians are near Berlin.”

“But there’s still Japan,” Merritt reminded them.

“I think war is stupid,” Richard said. “We ought just put the leaders of countries into a room and let them duke it out.”

Merritt thought it strange that such a “jock” as Richard would care about such matters as the war. He thought Richard would have been gung-ho to fight.

“Then we wouldn’t have to be drafted,” Merritt added. “And die”

Merritt’s thoughts went to his stepfather, Bob Casey, who was killed in the invasion of Tarawa. A tear came to his eye.

“What’s the matter, Merritt?” Richard asked.

“His stepfather died in the war,” Donna Mae said.

The evening was capped off as the four parked along the Lakefront parkway. Merritt and Dolores joined in some perfunctory hugging, while Richard and Donna Mae, obviously more practiced in “necking” were active in the front seat. There activities were cut short, as a police squad moved along side their vehicle, stopping and shinning flashlights into their car.

“Move along, kids,” came the order. The squad left quickly, heading to a parked car located several yards in front of them.

Prom night was over: Dolores looked exquisite in her dress, and Merritt survived nicely, thanks to the friendship of Donna Mae and the understanding of her date, Richard. Merritt realized he could be a “boy” and succeed. He felt good about that; yet, he told himself he’d have been a real beauty had he worn the dress.