Best Girlfriends Forever - 2

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Best Girlfriends Forever - 2


By Katherine Day


(Forty years after they met in high school, two boys – now living as women – rekindle their friendship and share their joys and struggles together. Copyright 2014. Edited by Eric.)

Chapter Four: The Poetry Club

Milton and Jennifer got together often during the last weeks of summer vacation. Some days they went on long, slow bike rides, while on others they met at the library and walked home together. Occasionally on their bike rides, they’d stop at the John Muir Nature Park, a wildlife area preserved in the northwest side of town along the Muskrat River, an ugly name Milton thought for such a lovely stream. They found a park bench in a clearing along a footpath that overlooking the waters of the Muskrat, which at that point flowed swiftly over exposed rocks. It was magical.

“This is my favorite spot,” Jennifer said. “I’ve written several poems about this place.”

“You have? You like poetry? Me too.” He smiled at the girl, whose eyes seemed to dance, magnified as they were behind her horn-rimmed glasses.

“You do? I think that’s so cool when a boy admits he likes poetry.”

Milton on an impulse reached over and put his hand on hers. As timid as it was, it was the first show of affection he’d ever made with a girl. She tensed, momentarily showing a bit of fear. She, too, had never had a boy touch her in such an intimate manner.

He felt her apprehension, and quickly removed his hand. “I’m sorry,” he said.

“No, don’t be,” she said, tears forming on her round face. “It’s just that I’m not used to being with boys.”

She reached over and grabbed his hand, pulling it over on to her lap, where they held hands. The hands of both were soft and moist. It felt awkward, and neither said anything for a moment.

“Do you write poetry, too, Milton?” she asked, obviously looking to change the subject.

“A little,” he admitted. “I like reading it, though. I read all of Shakespeare’s Sonnets.”

“All 154?” she asked.

Milton was pleasantly shocked; the girl knew that Shakespeare wrote 154 sonnets. He nodded “yes,” he had read them all.

“Well some I skimmed,” he admitted.

“But still. That’s impressive.”

“Okay,” he said. “Who is your favorite poet?”

“Oh, I have several,” she began. “I liked all of Elizabeth Barrett Browning’s poems, I guess. But, maybe John Keats is my favorite.”

“I like both of them,” he smiled.

She smiled back, a sweet smile that brightened her face in such a manner that her normally plain looks became beautiful to his young eyes.

“How do I love thee? Let me count the ways,” he said, suddenly quoting one of Browning’s most popular love poems.

“I love thee to the depth and breadth and height . . .” she added, picking up the second line of the poem. Together the two recited the poem, staying perfectly in sync with each other’s cadence:

“. . .My soul can reach, when feeling out of sight
For the ends of Being and ideal Grace.
I love thee to the level of everyday's
Most quiet need, by sun and candle-light.
I love thee freely, as men strive for Right;
I love thee purely, as they turn from Praise.
I love thee with a passion put to use
In my old griefs, and with my childhood's faith.
I love thee with a love I seemed to lose
With my lost saints, --- I love thee with the breath,
Smiles, tears, of all my life! --- and, if God choose,
I shall but love thee better after death.”

It was a sweet moment and Milton had a sudden urge to lean in to kiss the girl sitting next to him, but he was afraid that Jennifer would reject him.

They finished the poem in unison, and both looked at each other. Suddenly they both laughed.

“Wasn’t that a poetic moment?” she said finally.

He nodded.

“I was thinking of starting a poetry club in high school this year,” she said. “I wonder if any other kids would join up, or would they think it’s too square or old-fashioned?”

“I don’t know, but I’d join,” he said.

“Would you? That’s hot, but you might be the only boy.”

“So what? I’m already a loner.”

*****
In October, the first meeting of the Browning-Keats Poetry Club was held during the lunch hour in the classroom of an English teacher, Mrs. Harriet Delaney, who would be sponsor of the group. Milton agreed to come and when he walked into the room he saw eight girls plus Mrs. Delaney jabbering animatedly. As he entered Milton noticed the conversation stopped as the girls all looked in his direction. Suddenly shocked by the attention, Milton was about to turn and walk out.

Jennifer broke the silence by announcing: “This is my friend, Milton Lester. He’s read all 154 of Shakespeare’s sonnets.”

“Wow,” one girl said.

Milton took a seat next to Jennifer and they two engaged in close conversation before the meeting started. Just as they were about to start the meeting, the door opened and another boy entered the room. He was slender with long, flowing black hair that went to his shoulders. He had a thin, pretty face.

“Welcome,” Mrs. Delaney said to the newcomer, motioning to an empty seat next to her. “There’s a seat here, young man.”

The meeting started with each person introducing themselves; it appeared they all were either in their first or second year of high school.

The boy introduced himself as Adam Strawbridge, also a freshman. His said his name softly, almost with a lilt and in a high register. To Milton, the boy’s voice sounded much like a girl’s, but he put the thought aside since obviously the boy’s voice hadn’t changed yet. Nonetheless, this boy intrigued Milton. Little did he know that it was a beginning to a sweet friendship.

*****
Since Jennifer had organized the club with the help of Mrs. Delaney, it was only natural that Jennifer would be elected to lead the club.

“Let’s name her the poet laureate of Walt Whitman High,” Milton suggested.

“What a cool idea,” agreed one of the girls, a tall, stringy girl who wore no makeup, and tied her hair in an old-fashioned bun.

The others all agreed, but Mrs. Delaney warned them that she’d have to run the idea past the principal; she wasn’t sure the school was ready to have such a person identified with the school.

“Well, at least we can consider her our poet laureate,” the tall, stringy girl said.

They all applauded.

The group agreed to meet on Wednesdays during lunch hour; Mrs. Delaney arranged to reserve a small meeting room that adjoined the cafeteria where the members could meet and bring their lunches and eat while they met. Each week, it was agreed, one of the members would read her/his own poetry, while another would read something from the featured poet of the week. All members were urged to do some independent research on the particular poet and be prepared to discuss that poet.

The one problem with the meeting room was that it had glass windows that looked out upon the cafeteria permitting other students to look in at the group. Milton had seen several groups of boys walk by and make fun of the group; several seem to look directly at Milton and he watched their mouths moved, saying something obviously derisive of the scene showing two boys among the girls. He thought he could lip-read the words “queer” and “gay” from some.

Jennifer had suggested Elizabeth Barrett Browning be the featured poet for the next meeting of the club and announced that Milton would lead the discussion. “He’s already an expert on sonnets,” she told the group.

“Wow,” said the same girl who had made the “wow” remark earlier. Without saying it, Milton felt the girl must have been reflecting on how odd it was that a boy would be enthralled by the sonnets.

Jennifer walked with Milton as the meeting ended and asked, “Does that sound like we’re asking too much?”

“I don’t know, but it sounds like fun to me,” he said, then quickly added. “But that’s just me and I’m kind of weird anyway.”

“Well, we’ll see who drops out at the next meeting,” she said, her eyes taking on a mischievous glint. “At least there’s you and me.”

*****
Milton was curious about Adam Strawbridge; the boy said little during the first meeting of the Browning-Keats Poetry Club. The boys had no classes in common and in the school days that followed Milton only saw Adam from a distance, always alone and walking with his head down. He seemed sad and reflective.

Milton was happy that Adam showed up for the second meeting of the club and then clapped eagerly when Milton finished reading several of Elizabeth Barrett Browning’s sonnets, plus one of Shakespeare’s. He found the life of the poet to be intriguing and interesting, and he gave a full outline of her biography, prompting much discussion.

In reading the famed: “How do I love thee?” sonnet, Milton realized that he was looking directly toward this new boy, Adam. It shocked him so that he paused for a moment before heading toward the second line, “Let me count . . .” He quickly averted the eyes of the other boy, and looked toward Jennifer, continuing on and eventually projecting to the whole group.

After the session, Jennifer praised him for the “theatrical pause” he used during the sonnet.

“That was so dramatic, Milton, and then you looked right at me,” she said, her round, sweet face beginning to redden.

Milton didn’t know what to say; he had not meant to indicate any particular affection for Jennifer. He had come to enjoy her as a friend, but since he was so inexperienced at having a “girlfriend” he had no thought that perhaps this warm, friendly girl might be his first girlfriend.

Adam suddenly joined the two of them as they walked down the hall, coming up breathless behind them.

“Hi Adam,” Jennifer greeted the slender boy with the pretty face and long hair.

“I just wanted to tell Milton that I’m glad he joined the club,” Adam said. “I was afraid I’d be the only boy.”

“We’re all glad to have you with us,” Jennifer said cheerfully.

Milton smiled at Adam. “I’m glad you’re here too, Adam.”

Milton felt a strange kinship with this slender, rail-thin boy, and he knew it went far beyond the poetry they both seemed to enjoy. Just then the warning bell rang, giving them three minutes to get to class.

“Guess I better get to my next class,” Adam said.

“Want to meet after school, Adam? Jennifer and I are walking home together,” Milton said on impulse.

“Which way do you walk?” he asked.

“South, toward Grand Avenue.”

“Cool, I’ll meet you if you want,” Adam said, darting down the corridor to the right to his next class.

As he left, Jennifer looked darts at Milton: “What was that for? Why invite him? We don’t even know him.”

“I don’t know,” Milton said. “He just seemed so lonely. He’s new here.”

“OK,” Jennifer said, her momentary scowl turning into her usual sweet smile. “You’re right. Adam looks like he needs some friends.”

Jennifer took his hand and squeezed it affectionately. Milton noticed the girl’s hand was moist and warm; it was obvious she considered Milton to be her boyfriend. The idea scared Milton and he had trouble concentrating on Mr. Ethridge’s social studies class, even though the topic was one that particularly intrigued him – the lives of the early settlers in the United States. He wondered about how he was going to deal with Jennifer’s growing signs of affection, but it seemed that the greater amount of his attention fell upon a lovely boy named Adam; he was so pretty he could have been a girl.

Chapter Five: A Daring Proposal
It had become a tradition in New Bergen for high school students to attend a city-wide night of dancing, socializing and fun on the Saturday night of Halloween week.

Sponsored by the local Rotary Club and supported by the School District, the teens were encouraged to dress up in costumes. The annual event had been started more than 20 years before in 1948, just after the end of World War II following a Halloween night that turned into mayhem when teens conducted all sorts of mischief, some of it destructive.

“Teens realize they’re too old for trick or treating,” commented Dooley McFinn, the President of the Rotary Club at that time. “Let’s create something that they might like doing.”

Thus it was that the town’s modest sized arena was turned into a teen club on that night. Bands composed mainly of high school musicians played the “big band” music of the post World War II era while boys tended to line up on one side of the large room and girls on the other, slowly beginning to mix and start filling the dance floors as their hormones took over their shyness. Teen committees decorated the room and set up tables to serve soft drinks, punch, popcorn, hot dogs and cookies. It took a few years for the event to become popular, but eventually it captured the attention of the youth, and the event became a “must” for most teens. Fears that the event might turn into an orgy of sex, drunkenness and mayhem were thus far not realized. While supervision by adults (including police officers in plain clothes) was noticeably apparent, the event was kept loose and largely unstructured.

Now in 1969, when young men about to graduate high school faced the prospect of being drafted into the Armed Services and possible service in the dangerous jungles of Vietnam, high school boys had become an unusually serious lot, realizing that they needed good grades in order to get into college and thus possibly be exempt from active service.

The costume contest that was held at 10:30 p.m. had become a highlight affair. Prizes of portable radios, 45 rpm records and LPs were offered in various categories, such as for the “Funniest,” “Most Outlandish” or “Most Authentic” costumes. Youth clubs and school classes were encouraged to sponsor several contestants for the prizes, creating more interest throughout the city’s two public high schools and the sole Catholic high school. In the contest, the candidates would be marched across the arena stage while a cadre of judges, including the City’s Youth Council president, a representative of the local Boys and Girls Club, two faculty members from the local college and the director of a community theater group, would decide the winners in each category.

Most of the girls wore something, while many boys felt it was beneath them to do so or was sissyish and refused to participate. A few boys competed, of course, and in some cases, they wore something outlandish. It was not unheard of for a muscular, hairy athletic boy to appear in a tutu, purposely looking ridiculous.

This year’s contest offered a special “Talent Prize,” which would be given to the costumed student who performed a skit, reading or song lasting less than two minutes. Such participants had to be sponsored by a youth club or school class and be registered in advance.

“Our club should enter someone in the contest,” Jennifer Ashton suggested at the mid-October meeting of the Walt Whitman High School’s poetry club, named the Browning-Keats Club.

“Our whole club should go to the event,” Milton Lester said, one of two boys in the club of ten students.

“No way,” protested Natalie Thompson, a girl who rarely smiled. She was rail thin and claimed she was a vegetarian – which appeared to be true given her slender body.

“Why not?” argued another girl. “Don’t be such a stick in the mud, Steph.”

“It’s so silly, besides I wouldn’t know what to wear. I hated trick or treating when I was a kid.”

“Not everyone has to do it,” Jennifer offered. “Just those who want to.”

“I’ll tell you what. Why don’t we each dress up in the outfits of our favorite poet?” Milton suggested.

Natalie considered the suggestion for a minute. She was serious about her poetry and desperately hoped to become an English teacher or maybe a librarian. Besides she dreamed of being a famous poet herself, an avocation she practiced by filling her diary with poetry.

“That’s not a bad idea,” she said, a smile developing across her usually dour face. “I could come as Emily Dickinson.”

“Cool, you’d make a perfect Emily Dickinson,” Jennifer said. “She was a stoic one, she was.”

The group giggled, and soon the rest of the girls in the club had announced who their favorite poets were and said they’d try to replicate their outfits. Milton and Adam – the only boys in the club – said nothing.

“How about you guys?” Jennifer asked.

Milton was quiet and looked out the school window. He had told Jennifer many times that he loved Elizabeth Barrett Browning’s sonnets; thus she knew perfectly well who he liked. He could hardly dress as the early 19th Century poet, could he?

“Let us think it over,” Adam volunteered.

“It was Milton’s idea so he should at least tell us now,” Natalie said. “Certainly he knows who his favorite is.”

“That’s alright,” Jennifer interjected. “They can tell us later, but they should dress up like all the rest.”

Adam and Milton remained strangely silent as the meeting broke into a cacophony of chatter and giggling among the other members, all girls who were eagerly discussing the outfits they’d wear for Halloween. Several of them liked male poets, like Shakespeare, Walt Whitman, Lord Byron or Percy Bysshe Shelley, while others chose famous female poets such as Sylvia Plath or Sara Teasdale.

That afternoon, after school ended, Jennifer accompanied both boys as they went to their lockers and prepared to go home. The three left the school, heading down Highland Avenue toward their homes; they often walked to and from school together.

“You both have favorite poets,” Jennifer said, smiling.

“Oh, I’m not sure about mine,” Adam quickly said, hoping to head off further conversation.

“Really?” she queried.

“Well,” he said his voice hesitant. “I recently found Billie Holiday put great poetry in some of the songs she wrote. And she’s hardly considered a poet.”

Milton knew he had to get Jennifer off this line of talk. So often had he mentioned Elizabeth Barrett Browning’s sonnets that he could hardly disown the fact that she was his favorite.

“What are you doing Saturday, Jenny?” he said, changing the subject.

Jennifer made no attempt to answer Milton’s question, and refused to change the subject. She turned her attention to Adam’s reluctance to dress up as a black singer-poet.

“But if you don’t count Billie Holiday as a poet, I don’t know who I like, besides I’m not as dark-skinned as Holiday,” Adam protested, looking for an excuse to get out of the project.

“You’re dark-skinned enough so that shouldn’t make any difference,” Jennifer argued. It was true,

“But I’m not going to put on a dress. I’ll get laughed out of school.”

“Don’t be silly, Adam. Lots of boys put on girl’s stuff for Halloween, even the big tough footballers,” she said.

“Be a sport, Adam,” Jennifer pleaded. “It’ll be fine.”

“I suppose so,” he said, unconvinced by her assurances. “But who will Milton be?”

“Robert Frost,” Milton said quickly.

Jennifer burst out laughing. “That’s a good one. You know your favorite is Elizabeth Barrett Browning, Milton.”

“No way am I putting on a dress,” he protested, echoing Adam’s earlier words.

“Come on guys. There’s nothing wrong with wearing dresses just for Halloween. We’ll have so much fun.”

“But have you looked at how Elizabeth Barrett Browning dressed in those days, Jennifer?” Milton asked.

“I’ll never find outfits like that in just two weeks time.”

“Right,” Adam said, convinced that this revelation would convince Jennifer to quit being so insistent that they dress up as their favorite poets, particularly if they happened to be women.

“No problem. We can go to the costume shop that is used by the drama department at school,” Jennifer said. “The school has done plays set back in the 19th Century. I’m sure we can find something for you Milton.”

“Aw, come on, Jenny,” Milton said.

“And for Adam, I bet Mayala Jackson has something you could wear,” Jennifer said, referring to a tall black girl who was a club member.

“Aw, c’mon, Jennifer,” Adam said. “I could hardly ask her.”

“I know Mayala has something you could wear. Join in the fun, Adam. After all, it’s for the good of the club.”

“What did you get us into?” Adam said, turning to Milton, who had first suggested that they dress up as favorite poets.

“See ya’ girls,” Jennifer teased, turning left and leaving the two boys to continue down Highland.

At North 12th Street, Jennifer left the two boys and headed for her after-school job as a library assistant at the Emery Hinkle Central Library, where she mainly shelved books or assisted at the check-out counter.

*****
Adam and Milton parted from Jennifer, but had gone only a half block when Milton stopped. “Look Adam, I’m going to go with Jennifer to the library, OK?” he said.

“Sure, but why?”

“Just need to look something up,” he said quickly, leaving his friend and running after Jennifer.

He was out of breath when he finally caught up with Jennifer. He never was much of a runner and was panting heavily when he reached her.

“What’s up?” she asked, surprised by his presence.

“I need to look at some pictures of Elizabeth Barrett Browning,” he said, his chubby face growing almost crimson. It had been pink from the exertion of running after the girl, and now his admission that he was seriously considering the proposal to dress up as the poet caused him to blush.

“You’re going to do it! Marvelous, Milton.”

He nodded as the two continued to the library. Finally getting his breath, he said, “I thought why not do it? It’s Halloween and all that. And besides, if I’m going to do it, I wanna do it right.”

*****
“Oh, darling, that’s great,” Adam’s mother said when he told her he might be dressing up as Billie Holiday for Halloween, a decision he made while walking home. He decided that he’d dress up as Billie Holiday since he could more convincingly assume the part. Hadn’t he already sung some of Holiday’s marquee songs with his mother, usually dressed as a lovely jazz singer?

His mother’s reaction caught him off guard; he thought she would put her foot down and refuse to permit her son to dress up as a girl, thus giving him an excuse to get out of the obligation.

“But, mom, it’ll be so embarrassing,” he protested. “I only have a few friends in that school since I’m so new to town. They’ll think I’m some sort of weirdo.”

“Adam, honey, it’s just a Halloween thing. Girls will dress as guys and boys as girls that day. Don’t worry.”

“I suppose so,” he said, still not convinced.

“Besides, you make such a lovely girl, and you have such a beautiful voice. Will you be able to sing?”

Adam nodded. The contest rule said each club or homeroom entering the contest could choose up to three to represent their group, and each contestant could make a presentation of about two minutes long, giving him time to sing Holiday’s signature song, “God Bless the Child.”

“This’ll be fun, Adam. You just wait and see.”

“I hope so, but I’d rather not.”

In truth, Adam knew he was lying. He’d love to dress up prettily, since he knew that he indeed did look great in a dress. He should have known his mother would be in favor of him parading himself before the student body as a lovely girl. Hadn’t she encouraged him to dress at home, having him wear lovely gowns – the same ones that had hung unworn since his mother had quit singing professionally as a jazz singer?

Some the fondest times either had experienced were those moments when Adam donned one of her old gowns (he particularly favored a teal blue cocktail dress that ended at the knees and exposed his lovely shoulders and arms) and played the piano as his mother sang some of her old favorites. He soon was able to copy her sultry, jazz-style voice and sounded very much like the lovely girl he appeared to be in those moments.

Those moments, however, had been private ones; his mother often assured him no one else would ever know of their mother and daughter charade, even though she had set up a cassette recorder to preserve the memory. The reality of showing off his girly nature before a bunch of high school students did not sound like a wise option, but Adam soon realized he was excited by the prospect.

*****
“I’m too fat to be Elizabeth Barrett Browning,” Milton protested, as Jennifer and he were being led through racks of clothing hung in the shop of Costumes Galore, the costume house that worked with the high school drama department. The operator of the shop had offered major discounts for short-term use of clothing by high school students if authorized by the drama department. Jennifer, who did backstage work for the high school group, was able to arrange the visit.

“Don’t be silly, Milton,” Jennifer said. “You’ve trimmed down a lot and you have the same high cheekbones as Elizabeth.”

The two had taken a picture of the poet that Milton copied from the Encyclopedia Britannica to Theresa, an older lady manager at the costume shop, to guide the search.

“I’ve got just the gown for you, darling,” she said to Milton. “It was used in a Victorian drama that the Community Playhouse group staged just last month.”

Jennifer and Milton dutifully followed Theresa through the clothing racks, finding themselves in a sea of long skirted dresses, petticoats and other elaborate lingerie.

“This is our 19th Century section,” Theresa explained.

Milton was awestruck, finding himself fascinated by the lacy garments. As Theresa rummaged about the racks looking for the dress, Milton fingered the cloth of several gowns, excited by the feel of the gauzy cloth, realizing that he soon might be wearing a similar lovely piece of clothing. He felt a strange stirring of his emotions as his mind wrapped around the idea that he could look like a beautiful woman.

“Ah, here it is,” Theresa proclaimed, pulling out a white, heavily ruffled dress. “Come here young man, and let’s see how close a fit it is for you.”

Milton hung back, embarrassed by the idea that Theresa wanted to hold the dress up in front of him to check out the length and fit.

“Oh, Milton, just do it,” Jennifer said. “It looks perfect for you.”

He blushed but moved forward and held the dress up in front of him, as ordered. Jennifer and Theresa moved back and eyed him, their eyes scanning him slowly.

“It’ll work though he’ll have to wear a corset to bring in that tummy a bit,” Theresa said.

“Oh no, I can’t wear a corset,” Milton protested. “Maybe I can lose weight.”

“In ten days?” Jennifer laughed.

Milton nodded. He knew they were right. Even though he had lost some 25 pounds in the last year, he still had a chubby tummy and soft breasts like a girl. He had never been muscular, and his body frame could easily have been that of a girl, he knew.

Theresa sent Milton off to a dressing room, equipping him with a strange looking pair of briefs or panties.

“Take off all your male clothes, and put on these pantalettes to cover your boy parts. Then tell us when you’re done and I’ll come in and dress you the rest of the way,” she ordered.

“Pantalettes?” he asked, unbelieving his ears.

“Yes, now go on. They won’t bite. They were worn by women in the mid-19th Century,” Theresa said.

“You’ll find they’re most practical – even for a man – since they open in the front so that the woman would not have to remove her petticoats and other garments in order to use the toilet.”

Jennifer, hearing the exchange, giggled.

Dutifully, Milton did as he was told and retreated to the dressing room and removed his clothes. He tried to avoid looking at the full length mirror in the room where he’d have to view his sorry male body, his girlish breasts, soft tummy, small boy appendage and wide hips. The thought hit him hard: he looked like he could be a girl. He was intrigued by the pantalettes and noticed they were split in the middle. They were made of linen and resembled full-sized women’s panties that he’d seen, except that they reached several inches down each thigh, where he saw he’d use drawstrings to tighten the garment to the thighs. Similarly, a drawstring was used at the waist to bring the pantalettes together in the front.

Once he figured out how to wear them, Milton tied the drawstrings, and felt he was ready to summon Theresa to finish the task of dressing him. He paused for a minute, wondering if he should follow through on what suddenly felt to him to be a foolish enterprise. Finally, he stood before the mirror, folded his arms across his chest and looked into the mirror.

He was shocked by the sight: In the pantalettes, he indeed did look like a girl. His longish hair flowed down about his face and his folded arms had created a cleavage between his breasts.

“Are you ready yet, Elizabeth?” Jennifer’s voice sounded through the flimsy door of the changing room.

“I’m not Elizabeth,” Milton retorted.

He heard Jennifer laugh and then rap on the door. “I’m coming in,” she announced.

She entered before he could protest and he felt naked in front of the girl, covering up his bare chest as best he could.

“You look like a shy little girl standing there,” she giggled.

“Where’s Theresa?”

“She had to take care of a customer and she told me how to assist you.”

“I . . . ah . . . ah . . . feel so . . . ah . . . embarrassed . . . and . . . ah . . .”

“Milton, I’m sorry, I want you to enjoy this, and I really don’t want to embarrass you,” Jennifer said. “You’re my friend and I really think you’re so cool and brave to do this.”

Milton eyed the stack of garments Jennifer carried into the tiny room. “Am I wearing all of that?”

“Yes, Elizabeth, so we’d better get started,” she said, putting the stack of clothes down on the sole chair in the room.

“I’m not Elizabeth,” he said firmly.

“Well, right now you are. Don’t you like that name?”

Milton smiled. “Well, I guess I do. It’s a lovely name but it just seems to be so feminine.”

“That it is. That it is.”

The fitting began with Jennifer assisting Milton in putting on the corset, which tied in the back. It meant Milton had to pull in his tummy while she strained to tighten the strings in the back.

“I can’t breathe,” he said as she tugged on the strings.

“Theresa told me that you’d say that, but she said you’ll get used to it,” Jennifer said, her breathing hard because of the exertion she had extended to tighten the string ties.

“That’s if I live through this,” he gasped.

“There, I think that’s the best I can do,” she said, finally.

Milton looked down at his breasts and saw that the corset had pushed up the flesh so that they protruded even more distinctly than before. He saw Jennifer look at the effect of the corset on his body and nod approvingly. Looking in the mirror, he saw that the result was to make his hips look wider, giving him almost the classic hourglass figure so prized by young ladies. He blushed noticeably.

“I don’t think you’ll need these,” Jennifer said, removing the breast forms that filled the cups of a bra she held.

She reached around Milton, fitting the fleshy mounds of his chest into the bra cups, and linking the hooks of the bra from behind. Milton was mesmerized for a minute, stunned to see in the mirror how totally feminine he appeared to be. Jennifer put a white camisole over his head and put that in place, and then had him step into a fluffy petticoat.

“Now, we need to bring this dress down over your head, Elizabeth,” she said, instructing him to raise his arms over his head, as she slipped it on to him. “Great, it fits you.”

She brushed his long, straight hair, parting it in the middle, to match pictures of the poet they were able to find.

“Oh my dear Elizabeth, you’re a beauty,” she said. “No wonder Robert Browning was so attracted to you.”

Milton looked in the mirror. He smiled. Strangely, he felt comfortable, just as if he was meant to be in such a dress, even with its restrictions.

*****
For Adam, the choice of a costume was simple; his mother having been a jazz singer in her youth and with a closet full of dresses from some twenty years earlier meant she had quite a selection of dresses that could turn him into a reasonable version of Billie Holiday, minus, of course, the terrible addictions that plagued the talented woman.

“Oh darling, I think I’ve got just the outfit for you,” his mother said, while rummaging around her closet of largely forgotten clothes.

“Cool, mom,” he said, joining her in her bedroom. At first he exhibited reluctance about going through with the charade of dressing up as a woman, but he suddenly became more enthused. He felt that he could easily play the role of the famed singer.

“But, mom, that looks like it belongs on a little girl,” he protested, as his mother held the dress up against him.

“Look again at Billie’s photos. She seemed to favor these kinds of dresses.”

“Still, that big bow on the bodice. It looks so old-fashioned.”

His mother laughed. “Darling, you should know she sang in the 1930s and 40s and that was the style then. Now, get into the outfit and let’s see how it fits.”

The dress was a one-piece white dress with lavender polka dots; it had wide straps over the shoulders and a thin imitation leather belt. The bow sewn to the bodice was large and in stark white material. The skirt ended just at the knee.

“Oh, and I forgot these,” his mother said, holding up a pair of fingerless lavender cloth gloves that stretched to just above the elbow.

In preparation for the fitting, Adam had already put on peach-colored satin panties and a stuffed bra that gave him modest breasts. His curly hair had grown long and with his slender frame he knew he looked very much like a girl when in the undies. Shamelessly, he loved to look at himself when he was dressed in that fashion, demonstrating the poses that he presumed models used in presenting themselves in photo shoots.

His mother helped him into the dress and adjusted its fit once he had it on.

“It’s just adorable on you, darling,” she said.

Adam blushed as he looked in the mirror; it did look adorable, he thought. And, so feminine, too.

His mother smiled as he stood before here. Suddenly, her smile ended and her visage became puzzled.

“What’s wrong, mother?”

“Look at these pictures of Billie,” she said. “In everyone just about, her hair is heavily curled and put up. And you hair is hanging down.”

“No one in the contest will know how she did her hair, mother.”

“But, it’s just not Billie if we don’t do your hair right, Adam. We’ll have to remedy that.”

“How?” he asked, afraid what he suspected would be the remedy.

The next day, Adam’s mother arranged for an appointment at a salon, using a recommendation from a co-worker.

“You’re taking me where mother?” Adam asked.

“To a Christina’s Beauty Palace on Farmington Road,” she announced.

“But that’s for women,” he protested.

“Don’t worry, Adam, you’ll be dressed as my daughter.”

“I’ll be what?”

“We’ll give you a girl’s name for the day and you know you really could look like a girl,” his mother said, smiling.

Adam said nothing; it appeared he was doomed to go through with the project. In truth, he realized that he was often mistaken for a girl, due obviously to his slender form and moderately effeminate mannerisms.

“We’ll go to the salon after school on the Friday before the event,” his mother announced.

(To Be Continued)

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Comments

Best Girlfriend getting better..

Milton and Adam aren't actually straying into a girls domain; they are just surfacing as the people they already are. Milton even realizes he likes Adam. Jennifer is encouraging and pushing Milton; so what is her motivation?

Hugs, JessieC

Jessica E. Connors

Jessica Connors

Katherine dear, as I was.....

Reading this chapter, I started to get a feeling of "deja vu" ? Then I remembered from where, your Halloween story last fall! I assume this will continue past where it had ended ? Looking forward to seeing how they get to the beginning! Loving Hugs Talia

Alert reader

Yes, Chapters 5 and 6 are slightly changed from 'Elizabeth and Billie' which was published for the Halloween Contest. Perhaps the author (me) should have warned the reader of that.

And, yes, the story will continue on in three additional parts.

You're an alert reader, dear. Best wishes.