Chapter Four: The older sister

The idea that he could live as a girl excited Brian. It occupied all of his waking hours; he looked at girls in school and pictured himself in their skirts and blouses, and like them having a budding breasts just beginning to form. Already he noticed that his breasts were as large as any of the girls in his class, even those of his friend, Amanda, who had matured earlier than the others.

At night, he’d lay awake in bed, his thoughts building up into his intensity. Lying on his side, his breasts pressing together to form cleavage, Brain reached up with his hand to cup them, using his fingers to trace the crack between to two soft mounds of flesh. As he did so, he pressed his penis between his fat thighs and felt it grow.

“I could be so pretty,” he muttered to himself, his body beginning to rock and his penis growing harder. His fingers moved down to find one nipple that had also grown harder.

Suddenly, he felt warm moisture ooze between his thighs as he ejaculated, and he hurried quickly to restrict the flow of the sticky fluid, hoping not to stain the sheets, and reaching for a towel he kept close at hand. As he cleaned himself off, he felt a bit of remorse and some slight disgust with himself for thinking such thoughts. He wasn’t a girl. No, he was a boy, but such a poor excuse for a boy. What was to happen, he wondered?

He couldn’t help himself. It seemed to happen almost nightly now and always when he pictured himself as a girl.

*****
Amanda had a rather sheepish expression when they next got together for their two-on-two workout session, and her question came out haltingly. “Brian, can I ask you something?”

“Sure,” he said, puzzled by her uncharacteristic hesitation.

“You won’t get mad with me. It’s kinda personal.”

“Never with you, Amanda,” he said, with a smile.

“Well . . . ah . . . you know Janet Gleason, she lives on your block, I think?” she began.

“Yes, she’s nice,” he said, recalling the incident when he was shamed by Megan in the bike collision. Janet tried to be helpful.

“We were talking the other day . . . at piano lessons . . . we have the same teacher and walked home together,” she started.

He waited patiently for what was to follow.

“Now don’t get mad, at me or her, but . . . well . . . we both thought that we’d like to see you all dressed up like a girl. We think you’d be so pretty, and then we could go as three girls to the mall.”

“Oh, no!” he said, almost screaming it out.

“I’m sorry,” she reacted. “I shouldn’t have said anything. It’s just that you do have such a pretty face, and such a nice complexion.”

“Me? A pretty face? It’s too fat.”

“No it’s not, and with a little makeup, you’d be so cute.”

He blushed. He had looked in the mirror and wondered whether he had a face that could be pretty. It’s just that he had the beginning of a double chin, and that wouldn’t make a girl look pretty. And, he remembered playing with his longish hair while looking in the mirror, modeling it in a girlish style.

“Really?” he said, finally.

“Yes, really, Brian. Gosh, I hope you’re not mad at me for thinking that, or at Janet.”

“No, not at you or Janet. But it’s kinda weird. I’m a boy.”

“But you’d be so pretty as a girl.”

“Oh, Amanda, how could I be pretty. I’m too fat.”

“Not as fat as me, but look we’re both losing weight and you look so soft and with your lovely hair. It’s such nice hair, so long and flowing and we could fashion it to make you a hottie.”

“I couldn’t. What would happen if I got recognized? I’m teased enough now. Janet will tell you that. Timmy Merriman would never leave me alone. Or even Megan.”

“Come on, Brian, do it. Do it for me. We’ll have so much fun, and we can go to the Eastside Plaza, across town. Nobody we know will be there.”

“I don’t know, Amanda. Let’s just do our workout,” he said, changing the subject.

“OK, but think about it,” she said. “I got some lovely clothes that I’m too fat for and I think they’d fit you fine. We’re both about the same height and I’d love to see a pretty girl in them. You!”

He blushed, merely nodding. As he and Amanda puffed and groaned through their exercise routine, building up a huge sweat, he couldn’t stop thinking about being a girl shopping at the Eastside Plaza with two girl friends. He liked the idea.

*****
The following Saturday, after aerobics class, Brian accompanied Amanda back to her house. Amanda had persuaded Brian that they could dress him up, just to see how he’d look, and he had accepted on the promise that no one else would know. They were to be alone in the house, since Amanda’s mother was doing her duty at St. Rose’s Church preparing the altar for mass, as she did nearly every Saturday.

“I feel weird about this, Amanda,” he said as they walked together.

“It’s just for fun, Brian, you don’t have to do anything but let us make you pretty,” she said.

“Us? Who’s us? I thought it was just you and me.”

“Oh didn’t I tell you, Janet’s coming over, too.”

“Janet Gleason? Why her?”

“Her mom’s a beautician and Janet knows all about makeup and I don’t. Besides, she won’t say anything.”

Brian nodded, realizing he had two choices, run from the scene and lock himself in his bedroom, or go along with the girls’ plans. Why not try it, he mused?

*****
Amanda brought out several dresses that she said she hardly had ever worn, since she had grown too heavy for them.

One-by-one, they had Brian hold them up in front to get a quick look at how they might look. Brian was able to glance into a full-length mirror to also see how they looked, and soon was joining with the two girls in admiring each item.

“You have such nice outfits,” Brian said, as they completed the impromptu fashion show.

“And you looked so real modeling them,” Janet explained. She was, in contrast to both Brian and Amanda, slender, almost anorexic in body, and quite tall for a girl her age. She was healthy looking and was known to be quite athletic.

“Really.”

“I can’t wait to see how he’ll look in one of the dresses,” Amanda said.

“Me too,” Janet smiled. “Which is your favorite, Brian?”

Without hesitation, Brian pointed to a bright lavender-colored knit dress, which Amanda lifted up and asked Brian to hold it up.

“Perfect,” Janet said. “I liked that too.”

Amanda gave Brian a pair of purple satin panties and suggested he change out of his male clothes, and put the panties on. He already wore a bra, which he now wore regularly during workouts, a fact that the girls in the group had accepted without comment. One of the comforting things about being in a group of overweight kids his own age was that no one made fun of your body issues.

She also gave Brian a robe — it was obviously Amanda’s own robe, since it carried the scent of the soap that Amanda used — to wear when he came out of the bathroom.

The panties — a size 10 — fit perfectly and he looked at himself in the bathroom mirror seeing a girl with substantial breasts and ballooning tummy looking back. He smiled at the view, his desire to being a girl overriding any sense of shame he may have felt as a boy.

Returning to the room, the girls were awaiting, with Janet holding the lovely dress.

“Now turn around, with your back to me, Brian, and then take off the robe,” Janet ordered.

He did so and stood there awaiting instructions.

“Now let us slip this dress down over you,” she said.

She did so, and after a slight struggle in getting his arms through the proper opening, he was in the dress.

“Now turn around and let us see you,” Janet said.

“Oh my God,” exclaimed Amanda. “It’s perfect for you.”

“It is,” Janet added. “She’ll have the boys getting all excited.”

Brian heard the “she” pronoun, and blushed. “Let me see, let me see,” he pleaded.

“Just a minute, Brian,” Janet said. “We’ll let you see yourself in the mirror in just a minute.”

Janet busied herself, brushing down the dress with her hands. The action excited Brian as he felt her hands caressed the dress, which framed his soft body. He felt his penis grow hard, but knew that in its tiny size it would not show.

Janet then brushed his hair vigorously, smoothing it out, and letting it fall about his shoulders.

“Now, you can look,” she said, leading him by the hand to the mirror.

He was stunned by what he saw. There was no Brian to be seen, only a round, lovely plump girl, with dishwater blond hair framing her face. It was a sweet face. The dress was a halter style, with the bright, almost fluorescent, fabric rippling down her breasts which were prominent, due to a tie at the waist, which accentuate the natural curves of the body, including the broad hips. The dress ended at the knees, revealing a pair of truly lovely legs. Plump arms created an image of a warm, lovely girl.

“She’s so pretty,” Amanda said. “I can’t wait to get her made up.”

“Me either,” Janet said, “But we can’t keep calling her Brian.”

“No, we can’t,” the other said. She turned to Brian: “What name do you like? What girl’s name?”

Brian, still stunned by what he saw in the mirror, didn’t answer at first. He smiled at the image looking back at him. He did look like a sweet girl, he thought to himself.

“I don’t know,” he said, finally. “Brenda, Belinda, maybe?”

“I don’t know about those two names,” Janet offered. “Brenda seems like a name for an older woman and Belinda’s kind of a cute name, but just doesn’t sound right.”

“How about Bailey or Briana?” Amanda suggested.

“Bailey,” Brian said, leaping on the suggestion and almost squealing in delight. “I’m Bailey Kendall. How does that sound?”

“That sounds so classy,” Janet said. “You’ll be a girl with lots of class and good taste.”

“Oh this is so neat and so much fun,” Amanda said.

Brian looked in the mirror, did a slow turn around, mocking the manner in which models do their turns. He felt totally feminine now and finished with a curtsey.

“Bailey, you’ll be really hot when we finish with you, dear,” Janet said.

She pulled out a makeup kit she had carried in with her and ordered Bailey (the former Brian) to sit at the vanity while she pulled up a portable chair. They draped a towel over Bailey’s shoulders to protect the dress from spatters of makeup.

“We won’t overdo it, since girls our age shouldn’t wear too much makeup,” Janet began.

She used foundation first, working it into Brian’s face, following up with a bit of eye shadow to frame the eyes. She applied a bit of coloring to the cheeks, and then trimmed his eyelashes a bit, which worried him.

“Don’t trim them too much, Janet, since I’ll have to go back to being Brian, and I don’t want to look too girly,” Brian said.

“Don’t worry, no one will know later.”

She finished with a light lavender tinted lipstick and covered it with a satin gloss, giving the face a warm, soft glow.

“She’s just so lovely now, Janet,” Amanda said when they were done.

Brian loved what he saw now in the mirror and he stood up, enjoying the free flow of the dress about his thighs.

“What about shoes?” he asked.

“I think she should wear hose,” Amanda said. “And I have some new thigh-highs that might work for her.”

She went to a drawer, removing package, which when opened revealed a pair of sheer, coffee-colored stockings.

“Sit on the chair, young lady,” Janet ordered.

Brian obeyed, enjoying the attention he was getting now as a girl. It seemed natural to him as he held out his legs for them to assist in putting on the stockings. He loved how his legs looked in the stockings, slender and pretty, and with no ugly muscles to ruin the contours of his calves.

“Your legs below the knees are like a model’s,” Janet proclaimed.

“But my fat thighs ruin everything,” Brian said, his voice reflecting the disgust he felt for his flabby upper legs.

“That’s why this dress is perfect for you,” Janet said.

Amanda found a pair of ballet sandals that fit perfectly and Brian soon walked about enjoying being the girl he had finally become.

“The boys will drool when she walks by,” Janet said. “I wish I had those contours.”

Brian blushed, as he posed before the full length mirror. His girl friends had done a masterful job, turning his soft, chubby body into one with sweet curves, emphasizing the width of his hips, his lovely lower legs, and the protrusion of his breasts created through the pushup bra that showed cleavage. Even his tummy seemed not too noticeable.

Brian knew that many boys loved plump girls who weren’t too fat, and it seemed he would fill the desires of many teen boys. He smiled.

“Next Saturday,” Amanda said, “Let’s all three of us go to the mall — you, Janet, and you, Bailey.”

“You mean, I’d go as Bailey? No way,” Brian protested.

“Aww com’on,” Janet said. “Think of all the fun us three girls would have.”

“No way, what if somebody we know sees me?”

“Nobody could possibly see you as a boy when you’re all prettied up, Bailey,” Amanda persisted.

“Right,” Janet echoed. “But maybe we should not go to Westside Plaza mall, where all our friends go.”

“Maybe my mom will take us to Woodside Mall, nobody from school ever goes there,” Amanda suggested. “It’s so far away and is so ritzy.”

“We’ll have to dress real nice there,” Janet said. “They’re really fussy.”

Brian smiled at the thought. He had been spending lots of time recently looking at girl’s fashions in catalogues and fashion magazines, imagining himself as a classy, well-dressed girl. The more elegant he could be the better.

“What can I wear?” he asked. “Have you got anything for me, Amanda?”

“You could wear my First Communion dress,” she said, teasing him.

The three laughed at the suggestion.

“Don’t you have a nice plaid skirt for him, Amanda?” Janet asked. “With a nice white blouse and a cardigan sweater, she’d look divine.”

“I think we could find something for her,” Amanda said.

Brian did a little skip, showing his happiness at the idea, of being accepted as a girl. It just seemed so natural. What excited him, too, was the way his two friends so easily used the female pronouns and called him “Bailey.”

“I love you both so much,” he said, his voice high and lilting. It sounded so girlish.

*****
“You’re going to do what, Brian?” his mother was outraged when Brian told her of his plans to dress as a girl and go shopping with Amanda and Janet.

“Nobody’ll know, Amanda says. We’re going to Woodside Mall and nobody’ll know us there, mom.”

“But Brian, I’m not sure this is right for you to do. You’re my son, my boy.”

“I know, mom, but Amanda and Janet and I have so much fun together.”

“But, honey, I feel I’ve let you down,” Amy said. “You should be out playing football or doing boy things.”

Brian reddened, feeling a bit sheepish, and at a loss to explain why he so enjoyed being with girls and doing girl stuff.

They were sitting on a couch in the late evening of a school night when Brian finally got up the courage to tell his mother of the plans for the Saturday trip to the mall. It had become a custom to join his mother to watch re-runs of the 70’s show after the evening news. By then Marietta had gone to bed and he snuggled up to his mother, feeling secure against her warmth.

Both of them said nothing for a few moments; Amy put the television show into “mute,” since they had seen this particular version before. Anyway, neither was paying attention to the television set, each buried into reflection. Brian pressed more tightly against his mother and she put an arm around him, drawing him protectively against her. Brian felt so comforted.

“Ok, honey, I’ll let you do this,” she said finally. “But I want you to dress here at home. I want you to look like a proper young lady.”

He broke from his mother’s hold, and turned to face her, throwing himself into her arms and raising his lips to hers, kissing her eagerly.

“I love you mommy. Thank you, thank you.”

“Well if you’re going to Woodside Mall, you need to look proper, dear, and I don’t want any daughter of mine to not look her best.”

“Oh mommy you’re the bestest.”

“Maybe we’ll have to go and buy your some outfits for the trip,” his mother said. “None of my outfits are proper.”

“Oh you won’t have to mommy. Amanda has plenty of outfits and she’s outgrown some of them, but they fit me perfectly.”

“You’ve tried them on?”

“Yes, mommy, the other day at Amanda’s house. They said I looked hot.”

“Oh my God. Who are they?”

“Amanda and Janet.”

“Well, I need to call Mrs. Donatelli about this. She’s taking you to the mall, right?”

“Yes, mommy, and she knows about me. She was going to call you, but I told her I wanted to tell you first and then I’d tell her to call her.”

“I just wonder what she thinks about this business.”

“Oh I think she’s OK with it.”

“OK, honey, it looks like I’ve got another daughter,” Amy said, realizing that she had better make that appointment with the gender specialist soon.

*****
“Guess what?” Amanda said to Brian during the lunch period at school the following day.

“What?”

“The Fashion Girl store is having a showing on Saturday of fashions for plus-sized teens,” she said as she attacked the cottage cheese and peaches concoction she got from the lunch line in her latest effort to diet away her excess weight.

Brian had chosen similar foods; they both said they were on a starvation diet, and the most recent effort was only two days’ old.

“For girls like us,” he whispered so that only she could hear.

They both giggled. Between their aerobics exercising and their off-and-on dieting the two had lost a few pounds, and they claimed to both feel better. Yet, they could see no outward appearance of weight loss. That fact was discouraging.

“What do you say? The show starts at 2 p.m. Saturday. We should go,” she persisted.

“As long as Janet wants to,” Brian said.

“She’s cool with it.”

“I told my mom last night and she was mad at first.”

“Will she let you go? As Bailey?”

“Yes, but she wants to talk to your mom first.”

“My mom is not too happy with the idea, either,” Amanda said, “But she thinks you’re such a sweet boy. She wants to make sure your mom is OK with it.”

“Oh this is going to be so much fun, Amanda,” Brian said.

“Maybe we should celebrate with that brownie dessert with ice cream and whipped cream,” Amanda said.

“No, we girls have to watch our weight.”

*****
At the suggestion of Sylvia Henderson, Amy Kendall contacted the community’s leading Lesbian, Gay, Bisexual and Transgender agency for information about transgenderism; could her son be a candidate for eventually living as a woman, she was beginning to wonder. The literature she received was unusually frank and direct, telling of the pitfalls that face persons who may wish to transition; yet, it indicated that Brian’s tendencies might indeed be symptomatic of a person whose inherent makeup calls for such drastic steps.

She had watched him closely in recent weeks, and saw a girl inside him becoming more and more prevalent. She saw it in the way he walked, his feet straight forward and his stride tight and quick so that his hips even swayed a bit. When they sat together on the couch, he tucked his legs underneath his body as he leaned his body next to hers. And, in such a girlish fashion, he called her “mommy” now, just as his younger sister Marietta. He flayed his hands about as he talked, almost daintily.

She wondered, too, whether his growing femininity may be due only to his physical weakness and his soft body. She noticed his wide hips and his obviously weak arms and wondered whether that was motivating his more feminine behavior. He had always avoided playing with other boys, and she realized that he always felt at a disadvantage with them in their competitive games. How often had he come home crying because he was being teased for his ineptness, his pathetic physical strength?

Yet, he was getting good grades in school, seemed to enjoy helping around the house and becoming a great cook, with dinners always ready when she came home from work. Who could want more from a son? Or, a daughter?

Mrs. Henderson told her how pleased she was with Brian’s after school care for her daughter, Tamara. Brian had continued the twice-a-week practice of picking up Tamara, along with Marietta, at their school, and guiding them home, where he acted as a nanny for the afternoon. His enjoyment at caring for the two young girls was obvious; he joined in their games, giggled with them and even played “house,” where the always asked him to be the mommy.

“It’s almost like he could be a nanny,” Mrs. Henderson said. “I wouldn’t hesitate for a moment to hire him as a nanny. He’s such a lovely person, Amy.”

The two women had discussed Brian’s situation several times, and it was agreed he should be seen by a specialist to determine if the boy should be seriously considered a transgendered person. As a result, Amy made an appointment to see Dr. Wendy Ettleman the week after Halloween.

At first she was shocked with the suggestion that Brian would dress as a girl for a trip to the mall. Yet, the more she thought about it, the better the idea, since it would provide a test for whether he was truly inclined to live a female life. Besides, he’d be with two close friends and one mother, all of whom seemed to understand and appreciate the situation.

*****
Brian was surprised at the interest his mother took in helping him dress for the Saturday outing; she had stopped off at the Gourmet Fashion store and picked out some undies and a dress for him on Friday night.

“There’s no need for you to wear Amanda’s stuff, Brian,” she announced when she got home. She handed him two plastic bags with the pink Gourmet Fashion logo, and gave a similar third bag to Marietta.

“I’ve bought both of my girls treats because they’ve been so good,” Amy said proudly.
“You mean Brian’s going to be my older sister?” the little girl said.

“Just for tomorrow honey,” she said. “It’s for fun only, and you know you’re not supposed to tell anyone that Brian is doing this. Right?”

“I won’t mommy, criss-cross my heart and hope to die,” Marietta said. “Oh Brian will be so pretty, I just know it.”

“Yes, he will, dear, but just for tomorrow. It’ll be like dressing up for Halloween, dear.”

*****
At Saturday morning’s aerobics class, Brian puffed his way through the exercises, and though he had improved his activity level he still was unable to keep up with at least half the girls in the class. He still seemed to trail Amanda in the exercises, even though she clearly carried much more weight than he did. It was obvious, as a boy he was not as strong as many girls; it was embarrassing, and brought him to realize that he was ill-equipped to move into manhood. Doesn’t this just prove that he’s a girl, or at least should live as one?

His presence as the only boy in the class had weeks earlier ceased to be a novelty to the girls, or to Mrs. Goldsberry, the instructor. In giving directions, she long before had quit adding a reference to his presence and merely addressed the class while giving orders, with “Now girls . . .”

Indeed as he looked into the full-length mirror that lined three-quarters of the south wall of the exercise room, he could see that with his hair, tied in a bun and his bouncing breasts he truly was just one of the girls. He had even begun wearing leotards and tops that matched many of the girls and he had felt right at home. Was he not truly just one of the girls?

He and Amanda always worked out as a team, and it always amazed him that this girl, so round in the tummy and wide in the hips, could perform with such stamina and strength. She always encouraged him to do more, but never in an embarrassing way; always she stressed that a bit more effort would bring him quicker rewards as a “hot girl.” Her urgings were always done quietly so as not to draw attention.

This Saturday, the expectation of his travels to the mall as Bailey excited him and scared him at the same time. It would be his first outing as a girl, and in spite of the assurances that no one would see him as a boy underneath the skirt and blouse, he felt wary.

“Bailey,” she said softly while holding his legs for situps. “Gimme just five more on your way to a better waistline.”

He puffed through laboriously the last five situps, motivated by the pictures in his mind of what a lovely girl he could eventually become. He tensed up as he realized his afternoon’s adventure would be his inaugural as a girl in public.

*****
His mother surprised him when he got home after morning aerobics class.

“Get yourself showered and cleaned up,” she ordered as he entered the house, all out of breath and excited and scared about the upcoming trip. “Then I’ll help you get ready.”

In the bathroom, she had replaced their regular soap with a bottle of lovely scented body wash, which Brian applied to his skin, relishing in caressing his smooth, soft body. Silently he cursed his tummy, while enjoying the cushiony feeling.

“I smell so nice, mommy,” he said when finished and returning to his room, a towel tucked under his arms to cover his breasts, just as he thought a real girl would do.

“Here are your undies, darling,” she said, pointing to peach-colored panties and a matching bra that were placed on his bed. “I’ll be back in a minute, after you get them on.”

Brian had enjoyed the sensation of putting on a bra; he had learned to do, even hooking it in the back. He looked at himself in the mirror once he had put on the two garments, amazed at the image of a girl and her pinkish cushion of a body.

“Here, try this on, dear,” he mother said, carrying the dress she had bought.

“Oh mommy, I can’t wait to try it on.” Brian said, hugging her, like an excited teen girl.

She held the outfit up to display a grey and black sweater dress, cinched at the waist with kimono sleeves and a v-neck. She assisted him in putting it on and when he went to his mother’s room to look into her full-length mirror, he loved what he saw. With the pushup bra he was wearing, a bit of cleavage showed, and the dress went to the knees, leaving his lovely lower legs exposed.

“You look lovely, darling,” his mother said.

“I know mommy, and I don’t look too fat in it, either.”

“No, you look so nice, dear. Mommy is so proud of her daughter,” she said, kissing him gently.

His mother attached a black over the top head band, and then assisted him in putting on a pair of sheer natural thigh high stockings. Then he wore a pair of black ballet-style flats. His mother also helped him apply makeup, a neutral color lipstick with gloss and some light darkening of his eyelashes. She trimmed his brows slightly and finished off with a light application of foundation to add color to his plump cheeks.

“Now, there you are, my girl,” she said when done.

As Brian continued to prance about in front of the mirror, there was a sudden knocking on the door to the bedroom.

“Mommy, where’s Brian?” It was Marietta pounding on the door. “I wanna play with him, and I can’t find him anywhere. Mommy, why is the door locked?”

The pleas were insistent, and Brian and his mother looked at each other. His mother finally answered, “Just a minute Marietta, mommy’ll be out in a minute.”

“Where is he, mommy?”

His mother looked at him: “It’s Marietta. Do you want her to see you now?”

“Oh mommy, I’d hate her to see me like this?”

“But she’ll have to sooner or later if this continues. She’s your sister.”

“I know,” he nodded. “Better now, I guess.”

His mother unlocked the door, and Marietta bounded into the room, confused by the scene.

“This darling is your new older sister, Bailey,” his mother said.

“My . . . my . . . sister . . . Brian, you did it, whee,” the words tumbled eagerly from her mouth.

“Now this is between just us for now,” his mother cautioned. “Brian sometimes will wear dresses and be like a sister to you. He enjoys that and he likes being your older sister. You two can have all the fun you’ve always had.”

“Oh,” Marietta said. “That’s OK. I’d like an older sister.”

“That’s a good girl. Now don’t tell anyone, not even your friend Tamara, OK?”

“OK, mommy,” she said, running over to Brian and grabbing him jsutbelow the hips, hugging him. “I love you Brian, my older sister.”