Chapter Three: Brassieres

When he got home just before noon, Brian saw that his mother and Marietta were gone, leaving a note that they were shopping and would return about 2 p.m. His mother had come to trust Brian now to care for himself, including making his own lunch, so she hadn’t prepared anything for him to eat.

In truth, he was exhausted from the exercising and the bike ride home; he just wasn’t used to all that physical activity and he knew he would ache all over on Sunday, the next day. He went directly to his room to change into more comfortable clothes, but as soon as he had stripped down to his briefs, he collapsed on his bed, day dreaming about the hour he spent with the 15 girls, imagining he was one of them. He smiled as he lay on his side, his legs crossed and his one hand cupping and playing with a breast.

As he exercised he had felt his breasts bouncing and shifting as he moved, realizing his own breasts appeared to be larger than at least half of the girls in the room, including those girls who were several years older than he was and were beginning to mature. All of the girls, he noticed, wore bras, the younger ones in training bras and the others in sports bras.

After a few minutes of massaging his breasts, and growing more and more convinced in his mind that he was a girl, he rose and examined himself in the mirror, standing in just his briefs and without a shirt. Normally, he avoided looking at himself in a mirror, especially when he wore no shirt, afraid he’d feel shame at seeing his soft, pathetic body. Not this time, however, since he was reflecting on the image that he was a girl, seeing the hanging flesh of his breasts clearly outlined in his mirrored reflection, his narrow round shoulders and looking at his arms, relatively slender, but soft looking and without muscle tone. His eyes drifted down to his legs, noticing how fleshy they grew as they neared his crotch, but also see that his lower legs were slender and smooth and quite pretty.

“I need to wear a bra,” he said to himself.

He sat down on his bed for a minute to reflect on his situation. Maybe his mother had a bra he could wear, he thought.

Within a few minutes, he entered the laundry room and rummaged in the laundry basket, finding an older bra, a plain white one that she apparently wore around the house. He also found a pair of cotton pink panties. Quickly he put them on, but realized his mother’s bras were far too big; she was a large busted woman. He found a few socks in the laundry basket and stuffed them into the bra to fill out the breast cups.

In front of the full-length mirror in his mother’s room, he posed, excited to see that his image was that of a girl, about his age, with a soft, white fleshy tummy giving way to his wide hips and squishy thighs. He realized, too, that he had lovely facial features, full lips and cheeks that were framed in his longish hair. He brushed the hair back in a girlish manner, smiling at his image.

It was the first time he had ever put on female clothes and he found a new excitement stirring in him. For the first time in his life, too, he felt his penis growing hard and he seemed to have a spacey feeling.

He looked at the clock that now had turned to 1:45 p.m., just a few minutes before his mother and sister were to be home. He better change back to his boy clothes, he realized. Yet, the memory of those few minutes in his mother’s clothes felt so magical he knew it was just the beginning.

*****
“Mom, do you think I need to wear a bra sometimes?” he asked his mother later that afternoon, as they were both preparing supper.

“What? You, a bra? Boys don’t wear bras.”

“Yeah, I guess,” he said, taken aback at her rather stern tone of voice.

“Why do you ask, honey?” she said, more gently.

“Oh, never mind.”

“Something’s bothering you, Brian. You may as well tell me.”

Brian was sorry he brought the subject up, but he knew he’d eventually tell his mother about his feelings. He always shared his thoughts with her.

“Mom, you know I’m the only boy in that aerobics class?”

“Yes, does that bother you, dear?”

“At first it did, but now I like it,” he said, blushing. “The girls all seem to like me, and they’re all kinda fat or chubby. I guess I just fit in, like I’m one of them.”

“I’m glad you like it,” his mother said. “That class should be good for you, but what’s that got to do with having a bra?”

“Well, my breasts bounce around when we exercise, and I notice all the girls were wearing some sort of bra to hold their breasts,” he said.

“Won’t they tease you, dear?”

“No, I don’t think so mom. All the girls have their own issues with being chubby, so they would understand. Besides I could wear a loose shirt to hide the bra.”

“Are you serious about this, honey?” his mother asked, showing concern.

“Yes, mom, then I’ll be just like them,” he added.

“What?” she said in surprise. “You want to be like the girls there?”

Brian caught himself, realizing he had gone too far now in admitting his continued thoughts that he should be a girl. He loved the idea of being a girl, but wondered if that was a true feeling, or just some sort of passing fancy.

Amy completed peeling the potatoes and moved next to her son, pulling him into her arms and hugging him tightly. What was happening to her oldest child, she wondered? As she drew his soft body next to hers, she felt his budding breasts pressing against her and looked as his sweet face. He did indeed have girlish features, she thought, and worried about what was going on in the boy’s mind.

“Mommy, why can’t I be a girl?” he asked again.

*****
The following week Brian continued his regular schedule of picking up his little sister after school and walking her home. Two days a week, Tamara joined them and Brian watched the two of them until Mrs. Henderson came by to pick up her daughter.

Brian was already wearing his mother’s frilly apron and preparing supper when Mrs. Henderson rapped on the door. He waved her in.

“Did you like the aerobics class?” she asked.

He was cutting up onions and, as might be expected, was tearing up a bit.

“Yes, very much, except that I’m the only boy.”

“Oh, I’m sorry about that,” she said. “If that bothers you, you can quit and I’ll find you another class. They told me it was co-educational.”

“Oh it is, Mrs. Henderson, except that they only rarely have boys in the class, but that’s OK. The girls all seem nice.”

“OK, Brian, I’m happy to support you and I think the exercise will do you good,” Mrs. Henderson said.

“Oh and we’re getting a nutrition information there, too, since all the girls are fat, like me, and we need to lose weight,” he said. “In fact, I found this recipe for a veggie burger which I’m making tonight. I hope mom and Marietta like them.”

“I’m sure they will, Brian. Are you still going to bake those marvelous cookies?”

“Yes, Sylvia, but I’ll only be able to eat one of them. I save some for Tamara and you, if you like.”

“If I like? Of course, I like.”

Mrs. Henderson, besides paying for the aerobics class, paid Brian $20 a week for the two afternoons of watching Tamara. Brian found he enjoyed these afternoons the best, because Tamara and Marietta played so well together; often he joined in with them, but more and more he was becoming, in a sense, a mother to them. It was all feeling so natural. He was the woman of the house for several hours each day; he felt useful, wanted and a part of something sweet.

*****
After supper that night, Amanda called and suggested that the two get together after supper some night just to be friends.

“My mom can come and pick you up and we can play at my house,” she volunteered.

“I can walk,” he replied. “It’s not too far.”

“But it’s getting dark so early now,” she pointed out. It was October and the sun was down right at suppertime, meaning Brian would do the walk in the dark. He tried to insist that he’d walk over, since he didn’t want to inconvenience Amanda’s mother, but Amanda said firmly that his mother would pick him up. He finally agreed.

*****
On the appointed night, Amanda and her mother arrived in a huge, oversized SUV, and Brian had some difficulty climbing into the rear door, the step was so high.

Amanda’s mother was a round-faced, cheerful woman who had the same short, stocky body frame as her daughter. Brian could see the woman had a huge tummy that seemed to press up against her breasts as she sat in the driver’s seat of the car. Her hands held the steering wheel and her bare arms appeared muscular and powerful, not at all what you’d expect from such a short chubby person.

“Hello, honey, I’m Toni, ‘manda’s mom,” she said in a clipped tone that appeared to be a New York accent. “Call me Toni and I’ll call you ‘Bri.’”

“Nice meeting you, Mrs. Donatelli,” Brian said.

“It’s Toni, darling. I’m so happy you and ‘manda are friends. She’s talked about nothing else except you for three days.”

Brian grew red; what possibility could this girl see in Brian? Didn’t nearly every other kid in school look upon him as a sorry specimen of a boy.

“She said you bake good cookies, Bri, but you’ll have to prove to me they’re better than either mine or ‘manda’s. How dare you try to better an Italian mom when it comes to baking?”

She laughed heartily as she said this, and Brian could see she winked at him through the rear view mirror.

“Oh mother,” Amanda interrupted, showing some exasperation with her mother’s gushing behavior.

The Donatelli family lived in a large 100-year-old Victorian-style house that had obviously been restored; it sat back on a double city lot, facing a well-manicured lawn with tastefully placed flower beds, which had already been mulched for the coming winter.

Amanda told Brian that the Donatelli’s were longtime produce merchants in the city, dating back from when her great-grandfather came from Italy in the early 20th Century.

“You’re that ‘Donatelli’ family!” he exclaimed, recalling all of the produce trucks around town with the Donatelli name on them. “Wow.”

Amanda scoffed at him. “Brian we’re nothing special.”

“Still you don’t see any trucks around town with the Kendall name on them,” he said.

They both laughed.

What impressed Brian most in the house was the basement playroom that took over most of the lower lever of the house. It was well-appointed and lighted; on one end was a workout area, complete with a treadmill, stationary bicycle, and several weights machines.

“Who uses these?” he asked.

“We all do, but mom and me do a lot on them.”

He looked at this overweight girl with a puzzled expression. She didn’t look like she had ever done any exercise.

“Oh don’t let this fool you,” she said, jiggling her tummy with both hands. “I’m strong.”

“OK.”

“Really, let me show you,” she said. “Let me arm wrestle you, just to show you.”

“No that’s not necessary. I believe you.”

“Come on, it’s no shame to wrestle a girl,” she said.

“I suppose,” he said, and he agreed to the competition.

True to her word, Amanda was the stronger of the two; it took her about ten seconds to pin his arm.

“Oh you are strong,” he said. Actually in his mind, he knew how weak his own arm was, realizing the many of the girls in the aerobics class might have been able to pin him back just as quickly.

“This is just between you and me,” she said. “I shouldn’t have done that to you. I want you as my friend, Brian.”

“Me too, and I know I need to get stronger. That’s why I’m in the class. Do you girls think I’m weird being with all you girls?”

“No, most of us think you’re brave to join us,” Amanda said. “Maybe you can come over here and use this workout stuff with me. I’d like that. I need someone to work out with.”

She showed Brian the rest of the house, including her huge bedroom, which decorated in a strange mixture of dolls and photos of sports stars, both male and female stars. Her shelves contained several trophies from softball tournaments Amanda had been in; she also had a picture of her in a catcher’s outfit for the Tigers, where she was one of the few girls on a Little League team, yet was one of the best batters.

“I’m plenty active,” she confessed. “I just eat too much.”

“Me too,” he said. “Except I don’t get any exercise.”

“Now you will,” she promised.

*****
“We’re going to push you girls a bit harder this week,” Mrs. Goldsberry said in opening the second week’s session. “If you’re going to get anywhere close to being fit young ladies, you’ll have to sweat and work at it. Now let’s go to it.”

Brian blushed; it occurred to him that he was now lumped in with the group as one of the girls. Mrs. Goldsberry seemed not to notice anymore that there was a boy amongst the group. Should he protest? No, he thought, best to just keep it undercover. Besides, he sort of liked the idea of being just one of the young ladies in the class.

“Ready for the jumping jacks, young ladies!” the instructor ordered.

This involving jumping up, spreading the legs while simultaneously bringing the arms up over the head, a callisthenic that Brian found particularly tiring. The layer of fat that covered his body jiggled with each jump, his breasts bouncing heavily. He noticed with some envy that the girls, their breasts held tightly with brassieres, seemed to be having an easier time of it, spreading their legs farther apart than he seemed to be able to do.

“Spread those legs wide, girls,” Mrs. Goldsberry demanded as they continued into the fifth and sixth jumps.

Brian tried harder to spread them wider than he had been, but found he was falling behind the pace set by Mrs. Goldsberry and followed by most of the girls.

“Come on Brian, keep pace with the girls,” she ordered.

He grunted, nodding his head, trying mightily to pick up his pace, which he did a bit, and for which Mrs. Goldsberry smiled and said, “That’s great, dear.”

After 12 jumps, she blew the whistle stopping the exercise, and she said, “OK, girls, take two minutes rest,” and Brian almost collapsed as he sat on the floor, breathing heavily. Amanda plopped down next to him, breathing heavily but seeming to have an easier time of it.

“I hate those jumping jacks,” Brian said, his words coming out between gulps of breath.

“Oh but they’re good for us,” Amanda replied, her voice more even.

“I know,” he said, placing his right hand on his left breast, cupping it, as if to support it.

Amanda noticed his action, leaned over and whispered, “You know Brian, I bet you’d do better if you could have something to keep your breasts from bouncing.”

He blushed, nodding in affirmative.

Mrs. Goldsberry blew the whistle for the next exercise.

*****
The following Tuesday evening Brian biked over to Amanda’s house for their regular workout session. He both welcomed and disliked these sessions, welcoming them since he always enjoyed his time with Amanda but disliked them since they were so exhausting and somewhat humiliating since he couldn’t keep up with the girl.

He wore his workout clothes underneath sweatpants and sweatshirts, taking the outer clothes off for the sessions.

Amanda greeted him at the backdoor, leading him down to the workout room.

“Here I brought this for you,” she announced once they were in the room.

She held up a brassiere; it was a simple black one of fairly firm material.

“What’s this?” he said, not believing what he was seeing.

“I told you you’d feel better if your breasts were tied down, Bri’. It’s a sports bra.”

“For me? But I’m a boy.”

“Don’t be silly,” she said. “You need it for exercises. You’ll feel better with it on.”

“But . . . but . . .”

“Take off your shirt now and let’s put this on,” she commanded.

He did as she ordered, lifting his shirt up over his head, feeling so exposed. He hated taking his shirt off since he exposed his pathetically soft body, his breasts and his lack of arm muscles.

“How do I put this thing on?” he asked, holding it in his hand.

“Here, give it to me and turn around,” she said. “I’ll show you how to put it on.”

She had him put his arms through the straps, holding the cups of the bra tight against his breasts as she hooked the bra in the back. Amanda showed him how he could put the bra by himself.

“It’s a bit difficult at first,” she said, “But you’ll soon do it easily enough.”

Amanda was right. The workout session seemed to go much more easily for him now that his breasts were held in place and didn’t bounce around as he jumped and ran. When they finished, Brian was sweating heavily and felt totally exhausted. He was surprised that Amanda, however, who also carried some extra weight, seemed far less worn out.

Mrs. Donatelli invited her daughter and Brian to join her in the kitchen, beckoning them to sit at the kitchen table. She provided the two young people with glasses of lemonade and cookies (lo-cal, of course). Despite his fatigue, Brian felt good. He even felt like his arms and legs grew in muscular tone after the hour of workout, which was not possible, he knew. And for some reason, he felt happy and content, even though he was physically tired.

He was weary as he rose from the chair in the kitchen to begin his walk home, but Amanda told him to wait a minute.

“I want to give you something, Brian. It’s up in my room.”

“OK, what is it?”

“You’ll see,” and she bounded off to her room on the second floor.

Brian looked at Mrs. Donatelli, who merely shrugged her shoulders indicating she had no idea what Amanda was to get.

“How do you like all this exercising, Brian?” she said.

“It’s tiring, ma’am. I’m not used to so much activity.”

“It’ll be good for you, young man,” she said. “I could see you weren’t getting much activity.”

He blushed a bit.

“I got to take care of my little sister so much,” he explained.

“I know honey, and I wasn’t being critical. You’ve been good to both your sister and your mother, from what Amanda tells me.”

At that moment, Amanda rushed into the room, holding a plastic bag. She thrust it out to Brian, who grabbed it instinctively.

“What’s this?” he asked.

“Open the bag and look.”

He did. “Two brassieres. For me?”

“Who else, silly? You know you felt better tonight with the bra on when you exercised.”

Mrs. Donatelli looked shocked. “Amanda,” she demanded. “What are you doing giving this boy a brassiere?”

“Look at him,” she said, reaching over and tweaking one of his soft, breasts whose mound of flesh were framed against the tight fitting shirt he wore. “He needs it when he exercises, mom.”

Brian felt totally humiliated now, and wanted to run out of the Donatelli house, never to return. He wanted to lash out at Amanda, angered for drawing attention to his breasts; yet, he knew she was right. He did need the brassiere when he ran about and jumped during the exercise period.

“Amanda,” her mother said firmly. “You’re being mean to him.”

“But, mom . . .” she began.

“That’s OK, Mrs. Donatelli,” Brian interjected, coming to his friend’s defense. “She’s right. I guess I do need it.”

“They’re clean, Brian, and I don’t wear them anymore,” Amanda said. “One is a sports bra and the other a training bra. Should fit you fine.”

Brian left the house, carrying the bag. He realized he wanted to get home quickly so that he could model the bras.

*****
“What’s in the bag, Brian?” his little sister asked as he bounded in the door.

“None of your business, Marietta,” he said, running up the stairs to his room, trying to shut his door before his sister could follow him inside. But he was too slow.

“Come on, show me,” she persisted, grabbing at the bag as he tried to hold it far away from her.

“It’s not for little girls to see,” he said, petulantly.

“I’ll tell mom that you must have drugs or something in there, and then you’ll see,” she threatened.

“Marietta, please, maybe I’ll show you, just quit jumping on me trying to grab the bag,” he pleaded. “Come sit with me on my bed, first and slow down.”

His sister did as he said, joining him on the bed. He put his arm around her, and said, “You know I love you, Marietta?”

“Oh yes, Brian, I know that, and I love you.”

“Good, now what I’ll show you must be kept between you and me and mom, OK?”

She nodded.

“And you can’t tell anyone else, right?”

“Right.”

He opened the bag, displaying the two brassieres, letting her pull them out and hold them up. She let them dangle from both her hands.

“Are they for you?”

He blushed, and nodded yes.

“They’re for girls,” she said.

“Usually,” Brian agreed, “But I kind of need them, I guess.”

Marietta giggled, and played with the bras, waving them gently in the air, saying “You could be my older sister, Brian, and we could have so much fun together.”

“We already have lots of fun together, Marietta, don’t we? Don’t I play dolls with you and stuff like that?”

She giggled again, smiling up at him. “Maybe you could dress up like a girl, Brian, and then be my sister.”

He laughed, excited by the thought, drawing his sister tightly against him, hugging her. Suddenly he was picturing himself in a dress, wearing sheer tan stockings and ballet slippers, looking sweet and demure, holding hands with his little sister, also in a dress and looking so lovely together.

“Maybe someday for fun,” he said at last.

“Now Brian, now, be my sister,” she said.

“No honey, I’m not ready for that yet, and besides I don’t have any clothes.”

“Oh Brian, please.”

“No honey, not now.”

“You could wear mom’s stuff,” she volunteered.

“No, not now, please go, I need to do my homework.”

“OK,” she said with a pout.

“Now remember, tell no one, OK?”

She nodded in agreement and walked out of the room, leaving Brian to his dreams of being a pretty teen girl.

*****
As Brian, Marietta and their mother sat down at the supper table that night, the first words out of Marietta’s mouth were to reveal that Brian brought home to bras.

His mother’s face aimed a stern face toward Brian. “You brought home what?”

Brian blushed, finally answering, “Two brassieres”

“Where did you get them?”

“From Amanda, to wear when I exercise, mom. I can move much easier now. It’s just for exercising.”

“Oh honey,” she said, more sympathetically. “I guess that’s right. Are they new? Should you pay her something for them?”

“No mom, they’re old ones of hers, and she won’t take any money. I wore one today when were exercised. It works, and it held them in place,” he said.

Brian felt humiliated now as he talked about it, and his face reddened, at the thought that as a boy he had to wear brassieres.

Marietta, however, failing to sense the shame her brother was feeling, said: “I want Brian to be my older sister.”

“What?” their mother said.

“She’d be so pretty, I bet mom, and we could have so much fun as sisters.”

“Now get that thought out of your head, little girl,” his mother said. “Right now he’s your brother. Now both of you eat your supper and I’ll talk to you later, Brian. And you, Marietta, just don’t tell anyone about Brian and the bras, OK? Is that understood?”

The girl hung her pretty head, and said almost soundlessly, “Yes, mother.”

With his shame, however, came exciting thoughts of being a girl.

*****
“Brian, dear, do you like the idea of being a girl?” his mother asked him directly that night. She entered his room as he was preparing for bed, telling him to sit on the bed, while she took the chair from in front of his desk, pulling it opposite him. She had reached over, holding his hands in hers.

Brian for the moment seemed ashamed to admit he was seriously thinking about it, and feared what his mother might think. He looked down at his hands, being held so gently by his mother.

“That’s OK, honey,” his mother said.

“Yes, mom,” he finally admitted. “A lot.”

“I thought you did, darling,” she said.

“Are you mad, mom?”

“Oh my darling, not at all. It’s just that’s going to be so difficult for you.”

He started to cry, all the emotion of humiliation coupled with desires to be a girl mingled with his ineptness and weakness in physical activity boiling up within him. It now burst out anew, and his sobbing wracked his body, forcing his mother to move to the bed and take him in her arms, rocking him as if he were an infant.

When his crying subsided, she gave him a tissue to wipe his eyes.

“Darling, I’ve been thinking about this for sometime, and I’ve done some research,” she said.

“Yes, mom?”

“I think we’ll need to get you to a specialist, and I’ve contacted one in our hospital staff who deals with cases like yours, and he’ll be worth you talking to.”

“A shrink?”

“Sort of a shrink, Brian, but he knows about this kind of situation, and he’ll be discreet, of course.”

“Whatever you think, mom.”

He felt his mother’s hugs so warmly now, and that comforted him. He was loved and protected and maybe soon it would be as her daughter.