Jimmy's Training Bra
by Training Bra Boy (aka Amy Lynn)
Jimmy McSwain's life had been pretty rotten. In fact at at 11, it had been more filled with rotten that the lives of most people in their senior
years. He had grown up in a house with an alcoholic mum and dad where the living was just on the edge of poverty. The best present he had even received from them was a day of not being called stupid or useless, and that didn't happen too often. But that was all about to change.
Jimmy always did well in school, in fact, he loved school. He was bright and inventive and spent most of his time in the library reading. He loved to thumb through all the old magazines and even the libraries collection of old mail order catalogues. When he did that he say happy loving families, families that he wished his own home life was like.
It was a fateful night in the spring of 1968 when Jimmy's life all unravelled. The still of the night was broken by a load banging that shook
the whole house. Then before he knew what was happening he heard loud voices yelling, "Open up! This is the police."
The next thing he heard was scuffling, and a gun being fired. The loud booming voice of a police officer again rang out, "Drop the weapon! Drop the weapon!"
Then just as soon as it had begun, the scuffling ended and his bedroom filled with the light from a flashlight. The officer holding the
flashlight shouted "Hold your fire! I have a young boy in here."
Jimmy stated crying and the officer came over and comforted him. "It's okay, you're safe now."
The officer reached over and called out over his radio, "We have a young boy, about 10..."
"I'm eleven," Jimmy retorted.
"Make that eleven. Call children and youth services."
"What happened?" Jimmy asked.
The officer looked at him and saw a very sweet boy, filled with innocence. He replied, "Your parents are under arrest for dealing in
cocaine and LSD. Do you know what that is?"
Jimmy knew all too well, having witnessed both his mom and dad in a stupor as the TV blinked mindlessly in front of them after channel 7 had
signed off for the night.
"Yes," Jimmy answered.
"C'mon then. We'll take you someplace where you'll be safe," the officer explained.
As Jimmy was led out of the house he saw his mom and dad leaning against the wall, handcuffed. They snarled at him. "Yeah, you go with the pigs you little bastard," his dad spat.
When they got to the police station a kind woman gave him some cookies, chocolate chip, and a big glass of milk. As Jimmy enjoyed his treat
another woman entered the room and spoke silently to the one who had given him the cookies.
"Jimmy, do you have an auntie Jenny?" the woman asked him.
Jimmy nodded yes. He liked his auntie Jenny. But he was never allowed to see her. There was a big battle between his parents and his auntie over where he should should live. Deep inside he wished that he could live with his auntie in her beautiful house on the lake.
Before the woman could ask him, Jimmy asked, "Can I go live with her, please?"
The woman smiled kindly at him and replied, "I think so."
Just then the door opened and there stood Auntie Jenny. She held out her arms and Jimmy ran her. She looked at him and said, "You'll be safe now."
Auntie Jenny then looked over at one of the officers with a pleading look in her eyes. Sensing this, the officer spoke up, "Just sign some papers and you can give this child the best night's sleep ever, and hopefully a better life."
That night Jimmy climbed into a big clean bed and the only sound that broke the silence was the far off honking of some geese.
As the days rolled on, Jimmy grew happier and healthier. The spring air filled his lungs and his cheeks grew rosy. Off in the city, a trial was
held and his parents where each sentenced to 50 years in a maximum security prison. The court quite happily awarded custody to his Auntie
Auntie Jenny was well aware that Jimmy had been deprived of the things that other kids lives where made of. She vowed that anything Jimmy wanted he could have. Nothing was too big or too unusual.
As before Jimmy spent a lot of his time looking through magazines and the old Alden's catalogues in his Auntie's living room. Now as he looked at them he knew that this sort of happy life could be his. The library in town also filled his days with wonder as he explored the world via all the books and archived magazines deep in its cavernous lower floors.
So, it was only a wee bit of a shocker when one day over breakfast, Jimmy asked Auntie Jenny for the most unusual thing he could ever ask for.
"Auntie Jenny?" he asked between bites of Captain Crunch cereal.
"Yes, my sweet one," Auntie Jenny replied.
Jimmy began stuttering and then the glow of a blush came over his face. "Can I have a training bra, please?"
This was one request that Jimmy's Auntie Jenny was not expecting. Nonetheless, she was not ready to dismiss his request out of hand.
"A training bra? Hmm, now tell me why you want a training bra?" she asked.
Jimmy put down his spoon and scrunched up his nose. "I think I need one."
Auntie Jenny's curiosity was now piqued. "Hmm. Alright, what makes you think you need one?"
Jimmy began to blush an even deeper red and he he stared down into his cereal bowl. The abuse that he took from his parents began flooding back and he began losing the courage he had built up. But he knew that he continue. A tear formed and then dripped in his milk and cereal.
His Auntie Jenny sensed this and got up from her chair. Stooping down next to him she said, "It's okay. You can tell me anything. And I will do
my best to understand and give you everything you ever want."
Jimmy sniffed, and then replied, "Okay."
He began unbuttoning his pajama top. As he pulled it the reason for his request was all to apparent, for Jimmy had what appeared to be two small breasts, not unlike those of a girl beginning to develop. Jimmy's nipples were quite noticeable as was the puffy dark pink of his areolas. His breasts, while small, where about he size of those you'd expect to find on girl his age. Auntie Jenny smiled at him and hugged him as the tears began to flow for both of them.
"Mum and dad saw them and made fun me and used to hit me sometimes. Dad sad I was worthless and a sissy," Jimmy said through his sobs.
Auntie Jenny held him close and through her tears said, "It's okay Jimmy. No one is ever going make fun of you again. No one will ever hurt you again. And yes, I will see to it that you get a training bra."
Jimmy smiled at her. "Really?"
Auntie Jenny smiled. "Yes! Really! And, you are not a sissy. You, my child, are very very brave!"
Jimmy gave her a big hug, and just kept saying, "Thank you! Thank you! Auntie Jenny, I love you!" over and over again.
"And I love you too, Jimmy. Now finish your cereal and then go take a nice warm bath. I have a few phone calls to make, and then we'll get you
all taken care of."
Jimmy's eyes grew wide. "You mean today?"
"Why of course I mean today. You need a training bra and there is no time like the present to make sure you get one," Auntie Jenny explained. "Now hurry up."
Jimmy began slurping down his cereal as his body coursed with excitement. He then hopped from his chair and dashed to the stairs. He paused, turned on a dime and ran back to his Auntie, and gave her a big kiss. "Oh thank you thank you" he gushed.
While Jimmy bathed, his Auntie called Stacia Markiewicz. Her real name was Anastacia, but everyone in town just called her Stacia for short, and everyone in town shopped for their children at her small store on Depot Street. Stacia knew of Jimmy's circumstances with his parents and always treated him kindness. Jimmy knew that she always had a nickel ready for him to use in her gumball machine.
As Jimmy came bounding down the stairs after his bath, Auntie Jenny was finishing her call. "Okay, we'll be there in a bit. Bye."
"Alright Jimmy, are you ready to go get fitted for you first training bra?" she asked.
"Fitted?" Jimmy enquired. He had just figured that you go a buy one off the shelf.
"Yes, fitted, my dear!" his Auntie explained. "We have to make sure that your first training bra fits you correctly and helps you to develop
properly. That's what a training bra is for."
During the drive to town, Jimmy grinned from ear to ear. It was the happiest he had ever felt. "I'm getting a real training bra of my very
own!" he kept thinking over and over again. Even the tinkle of the bell on the door as they enter Stacia's store seemed brighter and more filled
with glee. A musty but not unpleasant smell lingered throughout the store and warm sunlight filled it. Shelves stacked with Red Ball Flyer tennis shoes lined one wall and boys trousers the other. Toward the back of the store, though, pretty girls dresses were hung on racks and a display rack with the words 'Teenform - For the Prettiest Possible Shape to Be In' above it was filled with boxes of training bras.
"Good morning Jenny and very good morning to you, Jimmy!" Stacia sang out in greeting.
"Good morning, Miss Markiewicz," Jimmy replied.
Stacia turned and pulled down the blind on the door to the store after flipping over her sign to say 'CLOSED'. She them stooped down, "Jimmy, I want you to know how happy it makes me to a part of the very special day for you. It's not every boy who gets to wear a training bra like girls
his age, and even more so not every boy who gets a personalized fitting for his training bra too! You are very very special."
Jimmy smiled and said, "Thank you, Miss Markiewicz."
Auntie Jenny then spoke up. "Jimmy, why don't you go into the changing room and take off your shirt so that Stacia can measure you."
Jimmy did as he was told and when he returned he walked out with his arm covering his exposed chest.
"Now, Jimmy, no need to be shy," Stacia said reassuringly. "I've done this for dozens of girls your age. Place your arms at your side so that I
can measure you."
Jimmy blushed as Stacia began to measure him, first around under his budding breasts and then around right at the center where his nipples
Stacia consulted a small chart that she pulled from behind the counter and then smiled at Jimmy and said, "Yes you definitely do need to start
wearing a training bra. You are a 32 AA cup!"
Auntie Jenny smiled at him and then, even though she knew the answer but just wanted to build up Jimmy's confidence and pride, asked, "Is that good, Stacia?"
Stacia nodded her head and smiled as he replied, "Most definitely. He is developing exactly the way girls his age should and a training bra is
very appropriate for him to be wearing at this stage."
Jimmy stood in awe and wonder as the two women chatted. Stacia went over to the display rack and grabbed a box. She then turned to him and said, "I think we'll start you off right with this style - the Teenform Lucky Start." She then handed the box to Jimmy. Jimmy stared at the box and the image of the girl wearing it. His hands shook a little at the excitement of the fact that he was holding the box that contained his very own first training bra.
Auntie Jenny then chimed in to break the silence "Why that one, Stacia?"
"Well, the Lucky Start features Gro-Cups that will expand as Jimmy's bust develops," Stacia explained. "This is one of the ones that everyone his age starts with. We have some other similar ones that you'll want to buy for him so that he has several to wear."
At that point Jimmy spoke up, "You mean get to have more than one training bra?"
"Why yes of course, sweetheart. If you are going to start wearing a bra, you have to wear one every day from now on!" Stacia observed.
Jimmy's smile beamed like sunlight.
"Go ahead, open it," said Auntie Jenny.
Jimmy fumbled with the box and pulled out the bra. He held it tenderly in his hands as if it was a fragile treasure and then held it up to his
"You're going to need some help with learning how to put it on. I think I'll let your Auntie do the honors," Stacia observed.
Auntie Jenny lead Jimmy back the changing room. She stood behind him and had him stand facing the mirror on the wall.
Gently Auntie Jenny took Jimmy's arms and slid the his bra into place. He sighed a sigh sigh of happiness as the straps of his training bra glided up his arms and floated into place on his shoulders. The sigh turned into an ear to ear grin when Auntie Jenny fastened his training bra in the back for the image he saw in the mirror was that of his nascent breasts snuggled in the cups.
"So what do you think?" Auntie Jenny asked.
"Oh Auntie Jenny, I love it. Thank you Thank you!" Jimmy replied.
As she pulled back the curtain of the changing room Auntie Jenny called to Stacia, "Stacia, will you check Jimmy's bra for proper fit, please."
Jimmy watched intently in the mirror as Stacia adjusted the straps of his training bra and snugged the cups into place. Jimmy's smile turned to
frown though when he heard her say, "Oh wait. This will never do."
Jimmy felt a tear welling up and lump developing in his throat at the thought of having this precious gift now suddenly snatched from him.
Stacia grabbed another box from the Teenform rack and handed it to him. "You simply can't be wearing boy's underwear! I can see the yellow and blue stripes of the waistband of your Fruit of the Looms, and they will never do. Here's pretty pair of matching panties for you to wear."
Jimmy looked over at his Auntie for approval. She smiled and nodded. "Go ahead," she said as she motioned toward the fitting room.
As Jimmy stood into fitting room and undid his jeans, he felt a feeling of contentment course through him. He pulled off his briefs and tossed
them into the corner and pulled the panties up his legs. They were cool and smooth feeling. He was just about to pull his jeans back on when the door to the change room opened a crack and Stacia handed three articles to him.
"Here Jimmy, your Auntie Jenny says to try these on," Stacia said as she closed the door.
Jimmy blinked as he looked at dress, a slip, and pair of girl's knees socks.
A millions thoughts raced through his mind, for he never dreamed that all this goodness and happiness could be his.
As he pulled on his dress, Auntie Jenny knocked on the door. "Here let me help you," she said as she opened the door.
After she buttoned Jimmy's dress in the back, she called out to Stacia, "Stacia, would you hand me Jimmy's new shoes, please?"
Stacia handed Auntie Jenny a pair of Mary Jane's which she slipped onto Jimmy's feet.
He turned around to look into the mirror and smiled. Nothing had ever felt so right in his life.
As they walked out of the changing room, Stacia smiled sweetly at Jimmy and gave him a big hug. "There now, you look perfect. Isn't that better than those smelly rough old boy's clothes?" she asked.
Jimmy smiled and said, "Oh my yes. Thank you so much, Miss Markiewicz. Oh and thank you Auntie Jenny."
"Now, you need to pick out a second training bra, Jmmy," Auntie Jenny observed. "Which would you like?"
Jimmy looks at the assortment of training bras and his eyes grew wide. His hands ran over the rows of boxes and settled on a Bi-Flex Young Scene beginner bra.
"May I have this one, please," he asked politely.
"Of course you may," Auntie Jenny replied, "as well as a few more dresses and panties which Stacia and I have picked out for you."
Jimmy cheeks glowed as they had never glowed before as a smile lit up his face.
"Here, Jimmy. This is a little booklet to tell you all you need to know about wearing a bra and about taking care of your bras," Staci said as
she handed him the pamphlet. "Why not sit here and read it while we total up the bill."
As Jimmy sat and read it, he knew that life was now so very good. This was the way it was supposed to be and he know was happy just like
If you liked this post, you can leave a comment and/or a kudos!
Click the Thumbs Up! button below to leave the author a kudos:
And please, remember to comment, too! Thanks.