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The Girl He Could Be - Part 1
🕑 Added 2025-03-31 15:28:11 +0000 UTCIt was during one of those really depressing periods that he thought he would see what kind of girl he would make.
It was a Saturday morning, and he was home alone. His mother and stepfather were both working all day, and his sister had just left for the beach.
The day before, he’d been harassed again at school. He had just been standing out in the field, by the school, talking to one of the girls in his class, when three guys he knew came up to them, making wisecracks.
"Who’s the girl with you with Chrisy?"
Tim knew what was coming next. He had heard it a hundred times before.
"Oh, it’s pretty little Timmy. You’d look much more natural in a dress, Timmy."
The girl had walked off with the boys, laughing.
Tim was heartbroken. Even the girls, whom he felt closer to than the boys, laughed at him. He walked home with tears running down his face.
His mother didn’t understand: "It’s just a stage; you’ll outgrow it." His sister was no help at all. She teased him about his looks all the time. He absolutely couldn’t talk to his stepfather.
Tim had slept late that morning, and when he finally got up, he had to step over Bridget’s clothes to get to the bathroom. She had always been a slob when it came to picking up after herself, but she had outdone herself lately. Even their bathroom was a mess, with towels, clothes, and her underwear all over the floor.
Tim didn’t make a habit of picking up after her, but the mess really bothered him. He hung up the towels when he was finished going to the bathroom and carried her clothes back to their bedroom.
What prompted him to do what he did next, he didn’t know. He dropped the clothes on the floor with the rest of her things. A pair of her panties caught his eye. He picked them up, feeling the silky material. He was intrigued. After the years of harassment and teasing, he wondered to himself. He took off his pajamas and stepped into her panties. They fit him perfectly, and the silky material felt smooth against his skin.
Tim knew what he was doing was wrong, but he was fascinated. A bra lay on the pile of clothes, and he picked it up. Putting it on was awkward, but he managed to connect the two hooks in the back. It didn’t look right as he stared at himself in Bridget’s mirror. The cups of the bra lay flat and empty. He got out a pair of his white cotton socks from his dresser and put one on each foot. That looked better.
A thought came to mind. His sister, who had short blond hair, had once worn a brown wig for Halloween. He searched through her closet, finding it finally, up high on a shelf, in an old shoebox. Tim was careful to remember exactly where it had been, under several other boxes.
Sitting at Bridget’s dressing table, he tried it on. It took him a little while to adjust it, but when he finally had it on right, he agreed with the people who had teased him so much: he did look just like a girl. Tim was sitting there in the bra and panties, and he thought, What the hell.
He picked through the pile of clothes on the floor and found the black skirt and purple blouse his sister called her favorite. He and Bridget were close enough to the same height that the skirt, with its zipper in the back, came to just above his knees.
Tim had always been slender, and it fit his waist easily. It was actually a little big on him. He accidentally pulled the wig off when he pulled the blouse over his head. With the blouse tucked into the skirt, he sat and fixed the wig on his head again.
At the full-length mirror on his sister’s closet door, he scrutinized himself critically. Turning this way and that, he compared the way he looked to the girls he knew. "Not bad." He said out loud to himself, smiling at the girl who looked back at him from the mirror. Something was still missing.
He found a pair on the floor. Tim took off the skirt and very carefully pulled on a pair of Bridget’s pantyhose. If he snagged them, she might wonder what happened to them. He liked the way they felt against his skin as he walked around the bedroom, and when he sat in the chair, crossing his legs. He didn’t have to take off the skirt to pull on her short black slip.
A pair of her short black heels was a little big on him. He stuffed the toes and then walked around the room. It was difficult at first, but he got the hang of it before long. Tim tried on several of her outfits that morning before he decided he had better put everything away.
He probably had several hours before Bridget would come home, but he was really worried about getting caught. With everything back exactly where he had found it, he got dressed and left the bedroom.
He didn’t even want to be in there when Bridget got home. It was fortunate for him that he did because she came home not more than half an hour later. She suspected nothing, and Tim thanked God. He had taken a great risk, and while it had been strangely exciting, he told himself he would never do that again.
He would tell himself the same thing, every time, for the next few years. Once he did it and saw how natural he looked, he came back time after time to experiment secretly. Each time, he would swear to himself that he would never do it again. The anguish he would put himself through was horrible. Tim cried himself to sleep so many nights.
The first time he found the courage to go out in public, dressed up, was a few days after he was thrown out of the house.
The urge was so strong, and it seemed so easy now, with no one to catch him. He was still in mortal fear that someone would see him and say, "Look at that, a boy dressed up as a girl." Some uncontrollable urge made him go out anyway. Tim still wore his wig, even though his own hair was well past his shoulders.
His problem was that he had no idea how to style it, and he was afraid to try. If it didn’t look just right, he was sure it would give him away. Who could he go to to learn? Tim walked around the block in a pair of tight jeans and a silk camp shirt.
He had on his wig and a pair of low heels. He had spent several hours getting ready and an equal amount of time getting up his nerve to step out the door. He even waited until 10:00 at night to play it safe. When he got back, he fell into the chair in the living room, exhausted from the tension he felt. Never again, he told himself. A familiar phrase to Tim.
A couple of nights later, about the same time, he extended his walk to three blocks. His heart stopped when he had to pass a woman walking her dog. She said hello to him, as if nothing was out of the ordinary. Using the high voice he had practiced to perfect for endless hours, he returned her greeting, "Hello."
Tim had gotten away with it so far, and he was feeling just a bit of self-confidence. Buses were dimly lit at night. He had a bus stop on his corner. It took him downtown.
All the stores had been closed for an hour, and he figured he’d get right back on the next bus and go right back home. It worked fine. A couple of people spoke to him, and he answered them. He even had a five-minute conversation with a lady on the bus with two kids. He had to think fast when she asked him his name. "Tammy," he told her.
The trip did a lot for his confidence.
Tim had taken a big chance when he mail-ordered his wig. If the mailman had delivered it when he wasn’t there to receive it, he would have had a tough time explaining it to his mother and stepfather. His desire outweighed the danger.
He had been using socks to stuff his bra ever since he had started dressing. Now that he was going out of the house, he had called an order into Sears for a set of lifelike breasts, the kind that women who have mastectomies use.
He wasn’t there when they came to the apartment to make the delivery, so they delivered them to the local store. The store called that night and asked for the lady, Mrs. T. Brooks, who had ordered them. Tim collected his wits and, in his female voice, got back on the phone. "Hello." "Hello, Mrs. Brooks. Your order came in today, and it’s here for you whenever you can get in to get it." The woman was very polite.
Tim was thrilled. "I’ll send my son in for it tomorrow. Thank you."
"You’re welcome, Mrs. Brooks. Goodnight."
Tim went to the mall right after work. He had to race to get home and then to work on time.
He didn’t even have the time to open the box and look. It drove him crazy until he got home. They were everything he hoped they would be. He tried them on and tried on three or four blouses to see how natural they looked with them. He was completely satisfied. They even moved when he did. They felt and looked wonderful.
The pharmacy trip was his next adventure. He needed more cosmetics. He had no lipstick or lipliner. The foundation he had always used was his sisters’, and it wasn’t quite the right shade for him. Her blush had been the wrong shade, too. He wanted perfume of his own. Tim already had eye shadow, eyeliner, and mascara.
Tim stood outside in the shadows for a long time. He wished he hadn’t put on a skirt; it made him feel so vulnerable. It also made him look more feminine, and he felt that the more like a girl he appeared, the less people would notice him.
He was on the verge of turning around and walking home when a car pulled into the lot and shined its headlights on him.
He felt conspicuous, just standing there. On just an impulse, he headed for the door to the pharmacy. Once committed, he didn’t feel as though he could turn back.
The salesgirl offered to help him, but he thanked her, saying, "I’m doing fine." Tim didn’t even look up at her as he knelt before the display. He felt that somehow, eye contact would give him away.
He breathed a sigh of relief when she walked away. He was sure he would sound strangely ignorant if he asked for her help. It took him a few minutes, but he found what he wanted. He even bought a couple of pairs of clip-on earrings. He had one pierced ear, but there would be no way to explain to the kids at school why he had both ears pierced. None of the guys had done both.
Tim knew his face must be bright red as he stood at the checkout.
He felt as though his palms were dripping with sweat as the young girl rang up each item from his basket. The cashier was too busy looking at the stock number of each item to look at the girl on the other side of the counter. It wasn’t until she finished and totaled it that she looked her in the eye.
"Twenty-seven and ninety-three is the total." She announced it to the girl. As she pulled her wallet out of her purse, the salesgirl couldn’t help but notice how red she was. "Are you all right?"
Tim wasn’t surprised by the question. "I’m fine." He got out a ten and a twenty and handed them to her. "I ran across the parking lot; I thought you were about to close." It was all he could think of to say.
That sounded reasonable to her. Giving her the change, she smiled at the customer. "Thanks, goodnight."
Tim smiled back. "Goodnight." He wasted no time getting home. It was easier than he thought it would be, and again, he received no strange looks, even in the bright lights of the store. Nothing went fast enough. School and work dragged. He couldn’t wait to get home at night. Thursday was when he planned his boldest venture yet. It had to be a weeknight, and Thursday was the only night he got off from work early enough. Tim was home by six. He was ready by seven thirty. Tim was too nervous to eat anything. He stood inside his front door in his denim skirt and jacket. He wore a white cotton, short-sleeved blouse underneath.
He decided on sneakers and pale blue socks.
He had picked up those big exercise socks that the girls push down and bunch up, and he had laces to match. He took the laces out of his spotlessly white sneakers and replaced them with the blue ones. They looked enough like a girl’s sneakers that way; he would make do until he could buy a real pair.
He had his wallet in his denim purse that hung from the long strap over his shoulder. Tim’s hand rested on the knob for five minutes before he got up the nerve to turn it. He knew that once he stepped outside, he was committed. It was still light out, and there would be people and children around as he walked to the bus stop.
Tim felt fortunate that his door opened onto an alley. Someone might see him, but they wouldn’t know which apartment he came out of.
No one paid him any particular attention as he walked down the street to the corner. It was a warm October evening, but not so hot that it caused him to sweat. The perspiration he felt on his back was because he was nervous.
He went to one of the smaller malls in the next town. The bus dropped him off right outside Gaffer's department store. He summoned up all his courage and walked in as confident-looking as he could manage. He knew that he would have to show confidence to get away with it. It wasn’t easy to muster.
The lingerie department was the scariest place to start, and he decided that if he could get away with it there, he could get away with it anywhere in the store. Besides, it was right by the exit. Tim was thankful that no salesgirl rushed up to help him. He had a pretty good idea what he was after as he made his way between the racks.
Betty saw the brown-haired girl when she crossed the aisle and started looking through the racks of pajamas. She was too busy at the register to leave it. She looked like she knew what she wanted; she walked right to the nightshirts. The girl who was working the department with her tonight, Karen, was on break and would be back in a few minutes. The girl would have to fend for herself till then.
Tim found what he was looking for. It was a white satin nightshirt with tap pants. He guessed at a size small. With it over his arm, he looked around. Underwear was next. Tim wove his way between racks toward the other side of the department. The panties were spread out on tables.
He wanted a new bra too, so when he saw the sets of bras and panties displayed on a rack nearby, he turned and went directly to them. He knew the sizes, and it only took him a moment to pick out a white stretch bra, size 34B, and matching string bikinis, size 6. Tim wanted more than one pair of panties, so he went back to the display tables.
He knew if he took too long to pick anything out, a salesgirl would see him and zero in. He quickly found the right size and picked out a pair of pink and another pair of white bikinis. Stockings were next, pantyhose. Here he was going to have trouble. Tim had no idea about sizes.
He began reading the back of a package. He learned that the right size was based on height and weight. There was a different table on the back of each brand, and he was confused. "Oh, Karen. I’m glad you’re back." Betty was still busy at the register, and now there were two women and the girl who looked like they needed help. Karen could see why. "Which one’s first?" Karen asked Betty.
Betty pointed to "the girl over by the pantyhose."
Karen walked up behind her, not even thinking she might startle her; when she was only a few feet away, she said, "Hi, may I help you?"
Tim didn’t hear her coming; he was surprised, but he turned to her, still trying to look confident. In his well-practiced voice, he said, "Hi. Yes, I’ve never bought this brand before, and I’m not sure of the size. The package is confusing." Tim handed her the package. She didn’t look at him funny when she did. He picked up another package to look at; he didn’t want to look her in the eye.
Karen was used to the problem. Everyone had trouble with these size tables.
"Ok, let's figure it out. What do you weigh?" Karen guessed at 115 to 120.
"118," Tim answered.
"And how tall are you?" 5’7," Karen judged. Maybe less; she has a lot of hair. "5’6"." Why was she looking at his hair? He had pinned his wig. It shouldn’t have moved. He’d check in a mirror as soon as he could.
Karen traced across the table on the back of the package and found her size. The package in her hand was it. "You’re ‘average.’ Is this the color you wanted? This is ‘suntan.’" "I need two pairs of taupe., Tim said courageously.
Karen went directly to them. "There you are, Miss. Is there anything else I can help you with?" Karen handed them to her. She looked around and saw that one of the women had left. The other one was still browsing around.
Tim had done fine so far. "I wanted to find a pair of white lace-trimmed leggings." Karen thought to herself, That will be easy. I already know her size.
"Just follow me." She remarked in her bright and cheery manner as she made a bouncing turn and walked off. Tim did follow. He almost forgot to walk correctly. They passed a mirror on a column. His hair was fine. What was the girl looking at?
Karen walked right to them. "Which length were you looking for? Short, capri, or ankle-length?"
"Ankle length, please." She was holding what he was looking for. "They come two pairs to a package, one white and one black." Karen raised an eyebrow as if to ask, Ok?
Tim wasn’t about to argue. He figured most girls knew they were sold in twos. If he said he didn’t want them, she might think he was strange.
"That’s great." He reached for the package. Karen, seeing that her hands were full, asked, "Why don’t you let me take those things to the checkout for you?"
Tim thought, Ok. "Thanks." He handed everything to her and followed. Betty had just finished with her last customer when Karen approached the register. "Betty, would you ring these things up for the young lady?"
Betty looked up and met the girl’s eyes. She has the prettiest eyes, she thought to herself.
"Sure, Karen. How are you this evening?" Betty asked the girl.
Tim would have been happier without the pleasantries. "Fine, thank you." The young woman picked up the sleep set.
"This is lovely." She rang it up. She wouldn’t be caught dead in the underwear the young girl picked out, but then she wasn’t a pretty young teenager anymore. The leggings found their way into the bag last. Tim stood impatiently waiting as she rang up his total.
"That comes to forty-two dollars and fifty-five cents." Betty waited while the girl took out her wallet.
Tim had expected it to be over fifty. "Great." He handed the woman the money. He put the change back in his wallet.
Betty handed her the bag with her purchases. "Have a nice evening." "Thanks, you too." Tim was relieved to be getting out of there. He didn’t realize it until it was too late that he would have to walk right by the other salesgirl to leave the department. He would have picked a different route if he had noticed her behind the rack of bathrobes.
Oh, to be young again. Betty thought to herself. The girl had the bounce of youth in her step.
"Good night," Karen said to the girl with a smile as she passed. She thought to herself, it wasn’t that long ago that I was a teenager.
She envied the girl. "Good night, and thanks," Tim said pleasantly as he passed her. He breathed a sigh of relief when he was out of the department with his purchases.
That wasn’t so bad. What was next?
Comments
Brianna Demonet
Tim is getting more brave by the day. Hopefully Tammy will be a regular fixture in his life.
My Freeze
Tim or Tammy is becoming very confident, things are going well for this stranger in a strange land. Look forward to your next installment.
Amanda
This is very interesting. Tim is so courageous in negotiating people and shopping dressed as a young girl.😂💁♀️
