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#21
Kevin has a great shopping experience ahead of him; I just hope he is able to reign in the nerves enough to be able to enjoy it. They are all being really good about this and once he has his own stuff, he will reap so many more benefits. Not only will the clothing fit better, he won’t have the guilt of borrowing from his sister to ponder.
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#22
(11-14-2020, 09:19 PM)Bill Wrote: I do so hope that they let him be a baby girl as well .
That’s a good idea in my opinion as he missed out on that part of his life. Mom though, believes he may not want it, it may play out that way though, my bet is his family will help him experience that if he wants to - would be nice. 
(11-14-2020, 09:28 PM)Girlygirl Wrote: Kevin has a great shopping experience ahead of him; I just hope he is able to reign in the nerves enough to be able to enjoy it. They are all being really good about this and once he has his own stuff, he will reap so many more benefits. Not only will the clothing fit better, he won’t have the guilt of borrowing from his sister to ponder.
Absolutely true. His little family are turning out to be very sweet.
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#23
I'm subscribed!
I can't wait to read more!!
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#24
A little more, been busy lately and not a lot of time to write...

The next morning, the family had breakfast and Julie joined Lisa in her room as she got ready to go to her soccer game. “I’m going to borrow this dress for Kevin, OK?” Julie asked.

“As long as he doesn’t ruin it,” Lisa made sure.

“It’s just for a couple hours,” Julie assured her. She left and went into her bathroom to grab her curling iron and brush before going to Kevin’s room. Entering, she closed the door and laid the dress down on the bed before plugging in the curling iron. Kevin looked at the dress then at his mother.

Julie could tell he was nervous. “Come here,” she soothed, “let’s get your pajamas off.” She helped him out of his pajama top and shorts and noticed he was wearing his boy’s briefs. Stepping over to his dresser and opening his underwear drawer, she pulled out a pair of his panties. “We can’t have such ugly underwear on under such a pretty dress,” she stated. “These are much prettier, perfect for a girl like you.”

Kevin blushed, but otherwise didn’t react as she hooked her fingers in the waistband of his underwear and slid them down his legs. He stepped out of them, and then stepped into the panties she offered him. Julie picked up the dress and once again slid it down over Kevin’s body. After zipping up the back, she spun him around again and smiled broadly. “There’s my beautiful girl!” she exclaimed.

Kevin smiled back at her. He had enjoyed wearing the dress last weekend, and once again he was in it, feeling the material gently sway back and forth with his movements and the air playing around his legs. Julie once again curled his hair slightly to be a more feminine style. She instructed him to put on shoes and then come downstairs.

“But mom, Tim and Kristen and Lisa will all see!” Kevin was once again scared and nervous.

“They already know, and there is no way you would be able to keep this a secret from them for long anyway,” Julie explained. “Believe me, they’re going to see you dressed as a girl plenty of times. Now, don’t be scared and just trust that everyone will see what a pretty girl you are.”

Kevin gulped at the thought, but understood and busied himself getting shoes on. He sat down on the bed, pulled his socks on and then put on his sneakers, looking himself over in the mirror. The shoes could definitely pass on a girl, but the socks pulled up just didn’t look right. He scrunched them down around his ankles and thought it looked better. He heard his mother calling for him, telling him that they all needed to be leaving soon.

Kevin stepped towards the door and opened it slowly, making sure no one was there. He made his way down the stairs and slowly turned the corner into the kitchen. Lisa had been grabbing the last of her things for the soccer game and Tim was filling a water bottle for himself. Kristen was relaxing at the table while Julie finished placing the last of the breakfast dishes in the dishwasher. Everyone stopped and looked at Kevin standing there in the dress.

Julie hoped things would go well with everyone. It was a long moment before Tim broke the silence. “You look very pretty in that dress,” Tim said. “I think you’re a lovely little girl.” Kevin breathed slowly, afraid that he would still hear teasing from his sisters.

“You look cute, kiddo,” Kristen smiled at him. “I think you’re gonna need a couple more dresses though.”

“Just don’t ruin my dress,” Lisa quipped. Julie looked down at her and frowned. “You do look nice though,” she added.

“We need to run,” Tim announced, ushering Lisa into the garage to take her to her game. Julie dried her hands and started the dishwasher and stated that they too were ready to go. She and Kristen walked out to the car with Kevin in tow. He was nervous as he climbed in and buckled his seatbelt. Not only did his whole family just see him in the dress, but now they were going out with him dressed as a girl!

They drove downtown and parked across the street from the department store. Julie and Kristen got out right away, but it took Kevin a minute to get up the courage to open his door. Julie walked over as he did and took his hand. “Don’t worry,” she said quietly, “everyone just sees a pretty girl going shopping with her mom and sister.”

Kevin stepped out of the car and walked timidly toward the department store, holding his mother’s hand tightly. As they walked, Tim looked around, nervously to see if anyone was looking at him. They opened the doors to the department store and made their way over to the girl’s section. Kevin had been nervous before, now he looked almost scared.

“Like I said, sweetie,” Julie softly soothed, “everybody sees me with my lovely daughters. If you relax and don’t draw attention to yourself, nobody will know.”

The first place Julie went was to grab another package of panties for him and then look at the bras they had available. She picked up a bra and then handed both items to Kevin. He wasn’t sure what to do with them. “They’re for you,” she instructed, “you can carry them.”

Kevin looked at the two items intently. The panties were not much different from the ones he already had, but the bra was something new. He knew his mother and older sister wore bras, but Lisa didn’t yet. He hadn’t thought about trying one on at all and just stared at the fabric on the hanger. “K, sweetie, come on,” his mother’s urging broke him out of his focus on the item.

The trio walked over to where dresses were hanging on racks. His mother began to scan through them, occasionally stopping to look at one or another. “Any that you like in particular?” she asked Kevin. He came over and looked at them, running his fingers over the material of some, looking at the colors of others. “Girls have it so much better,” he thought to himself, “they get so much nicer clothes.” He stepped over to another rack that had a pastel pink dress edged with lace and light green bows on the shoulders. He couldn’t help but stare at it.

“Like the frilly things, huh, kiddo?” Kristen asked. Julie stepped over to look at what Kevin had settled on. “That’s very pretty,” she agreed, “let’s see if we can find one in your size.” She flipped through the clothes, holding one or another up to Kevin before deciding. She draped it over her arm and continued to look at others. She found another one in blue and white that she thought would be nice and draped it over her arm as well.

“Let’s go see how they fit,” she announced and walked towards the fitting rooms. Kevin was suddenly frightened. He had to try these on here in the store? Julie sensed his nervousness and crouched down to talk to him. “It’ll be fine,” she assured him quietly, “everybody here thinks you’re a girl. I’ll go in the fitting room with you and help you try them on, nobody is going to find out.”

Kevin looked around nervously and had to admit his mother was right. Nobody was paying attention to them at all. He had thought being a boy in a dress he would stick out like a sore thumb and everyone would be laughing or teasing him, but nobody had given them as much as a second glance. He meekly followed her into the dressing room.

Once Julie had shut and latched the door behind them, she turned to Kevin. “Let’s get that one off of you and see how these others fit,” she said. He turned around for her to unzip the dress he had on and let her lift it over his head. She pulled the pink dress off the hanger and slid it over his head and down his arms before zipping the back of it. She stood back and looked at him and just smiled. It was a fairly good fit, and she agreed that they would get it. She helped Kevin out of it and then slid the blue dress into place on him. Again, she was happy with the fit and helped Kevin back into the yellow dress he had been wearing.

As she placed both dresses back on their hangers, she spoke to Kevin. “I think that pink dress would look really nice with some white tights under it,” she began, “and I think you could use a nightie.” They exited the dressing room and went back to the girl’s section. “Why don’t you find a nightie you like while I get some tights for you,” she instructed.

Kevin went over to the rack of nightgowns and flipped through it. He found one with the puppies from 101 Dalmatians on it. It was white with black sleeves and a bottom ruffle in red with black spots on it. On the chest was one of the dogs with the words, “Mornings are Ruff,” under him. Julie came back with a package of tights and helped him find a nightgown in the right size.

Their last stop was in the shoe section where Julie helped Kevin find a pair of patent leather Mary Janes. He felt strange, looking down at the shoes, never having worn anything besides sneakers for as long as he could remember. The slick leather bottoms were going to take some getting used to.

They made their way to the cash register and Kevin just stood quietly behind his mother as she paid and they left the store.
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#25
Kevin’s first interaction with the outside world in a dress seems to have gone without incident (certainly better than he would surely have hoped) and he now has some of his own gear for what will surely make for more fun and undoubtedly more ethical activity at home. 

Hopefully this will make him more confident in the community and better prepared for a first face to face encounter with the uninitiated.
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#26
Kevin is very lucky to have encouragement and help for what indeed would be a very frightening experience. His confidence can only increase now. His new dresses and tights are gorgeous, though his shoes are perfect, will take a little getting used to.
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#27
I haven't been able to write much lately, I got some part-time work to keep me sane during retirement. With the holidays, I now have a chance to do more, so here it is...

Once they returned home, Julie helped Kevin take his new things up to his room. As they entered, Julie shut the door behind them quietly. She helped him pull things out of the bags and remove tags before putting them away.

“Lisa was good about letting you borrow that dress,” she started, “but I’m thinking it might be good to take it off so we can give it back to her. You’ve got your own dresses now, so I think it would be better to wear one of them, maybe that pink one you like?”

Kevin turned around to help his mother unzip him from the dress. “You’re going to have to start figuring out how to do these up yourself,” she suggested. Kevin slipped the dress off and handed it to her. “Your bra is something you will also have to learn to put on,” she said as she handed it over to him. “You can either pull it up your arms and then hook it in the back or put the band around your chest backwards and turn it around before putting your arms through.”

Kevin looked at the bra quietly. “Why did you get me a bra?” he asked, “Lisa doesn’t wear them.”

“She doesn’t yet,” Julie answered, “But she will about the time she gets to your age. Have you noticed that girls in your grade at school are starting to wear bras? I know that Kristen got her first bra at this age, so I thought that you should have one as well. Unless you want me to treat you like a little girl?”

“No, that’s OK,” Kevin shook his head quietly as he slid the bra straps up his arms and attempted to hook it behind him.

“Good,” Julie chuckled, “I wasn’t sure about going back to changing diapers again.”

“Mom!” Kevin protested, “It’s bad enough I have to wear them to bed…”

“It’s OK, I’m kidding,” she responded, “it’s not your fault that you need them anyway. You’ve got to remember they make them and sell them because it’s a common thing that happens. Heck, I used to make sure that there was protection on the bed with your father if he had a bit to drink because he would wet the bed as well.”

“Really?” Kevin was surprised. “I never knew about that.”

“He certainly didn’t want anyone to know about it,” Julie replied. “You know how he is always so big on ‘being a man’ and everything? I think it’s because he’s afraid of what people will think of him if they knew the truth.”

“I guess I can see that,” Kevin answered.

“Just remember that with how your father is, he won’t necessarily approve of you wearing things like this,” Julie reasoned, “so you might not want to let him know. Now, I think those white tights would look good under that pink dress.”

Julie handed the tights to her son and chuckled as he tried to pull them on like normal socks. “That’s not going to work,” she explained. “gather them up in your hands so you’re just pulling them on from the toes up your legs.” She helped him with one leg and then the other, finally pulling them up around his waist.

She stood by as Kevin pulled his new dress from his closet and watched him drop it over his head. “Can you get it zipped up by yourself?” she asked, watching and waiting to see if she needed to assist him with it. He was able to get it done, and she smiled at him broadly, amazed at how pretty he was in the new clothes. She picked up the dress he had worn shopping to take back to Lisa’s room, telling Kevin to put on his new shoes as she left.

He slipped on the new shoes and buckled them. Standing up, he looked himself over intently in the mirror. He was thrilled to see the reflection of a young girl smiling back at him. He had never thought things would happen like they had in his wildest dreams. For the last two years he had found looking at girl’s clothes irresistible, and would often sneak the weekly ads from the newspaper just to look at the clothes on sale and imagine himself in them.

Kevin marveled at the way the tights felt around his legs. The sheer material made a pleasant sensation as his legs rubbed together; it was electrifying. His eyes darted from one point to another on his body—from the shiny shoes to the bows on the shoulders to the lace on the hem of the dress to the little flip his mother had put in his hair. He had never known it could feel so good to feel pretty.

He finally broke free from the stare of the girl in the mirror and left his room. Going downstairs, he found his mother and older sister eating a light lunch. “Would you like a sandwich, young lady?” his mother asked. Kevin nodded and was soon sitting down with the two of them happily munching away.

Kristen soon broke the silence. “You really do look good in that dress,” she said, “it’s very pretty. Never thought we’d be seeing you dressed like this, but you do make a pretty girl.”

Kevin smiled at her and thanked her. “You do need to learn a bit about wearing a dress though,” his mother interjected. “You didn’t pay attention to what happened with the dress when you sat down and it bunched up under you, and you need to learn to sit with your legs together so you don’t show off your underwear.”

Kevin blushed at the thought of people looking up his dress. “It’s nothing to be embarrassed about,” his mother continued, “people are going to think you’re a girl as long as you don’t give them any reason to think otherwise. If you act like you’re a boy, they might figure it out, but if you learn how to act like a girl, they’ll never know.”

Kevin finished his sandwich as he thought about what his mother had just said. Kristen gathered the plates into the sink and headed to her room while Julie looked at Kevin intently. “So,” she asked, “the thing you need to figure out is if you want people to think you’re a boy wearing a dress, or do you want them to think you’re a girl? Because if you want to be a girl, there’s a lot to go along with that.”

It didn’t take much thought for him to answer. “It’s been fun being a girl, I want to be a girl!”

Julie wasn’t fazed by his response but realized there were more implications to how Kevin had answered than just acting the role he was dressed for. She definitely felt there was more that needed to be figured out for long term decisions, and she was going to have a long talk about it with Tim this evening. “Well,” she responded, “there’s some things you need to figure out, that’s for sure.

“First, when you sit down,” she continued, “don’t just plop down. That works fine in your shorts or trousers, but it scrunches your dress up under you and can wrinkle it. And unlike shorts or trousers, you can show off your panties easily. So when you sit down, sit back and down and if you need to, bring the back of your dress under your legs to control where it goes.”

Kevin practiced this a couple of times and it didn’t take a lot of effort, just a small amount of concentration on what he was wearing. “The more often you wear a dress, it just becomes something you automatically do,” Julie encouraged. “When you’re sitting you want to keep your legs somewhat together as well. If you spread them like when you’re wearing your pants you may end up giving everyone a peek at your underwear. Your sisters learned long ago about it since they’ve been wearing dresses most of their lives. You need to learn and practice it, so don’t get upset if you hear me tell you nobody wants to see your panties, your sisters got told them same things when they were little.”

Kevin blushed again and looked at the floor, slightly embarrassed. “It’s just something all girls learn, you’re just starting a little later than most,” Julie tried to calm him.

“I know,” Kevin said quietly, “it’s just that it’s embarrassing…”

“What’s embarrassing?” Julie asked.

“Hearing about my,” Kevin quieted down, “my panties showing.”

“Sweetie, don’t be embarrassed,” Julie soothed, “if you want to be a girl, this is what it is. Girls wear panties, so you should be proud to wear your panties and be a girl! You’re wearing a beautiful dress, be proud of it! I mean really, is there anything wrong with being a girl”

“No,” Kevin admitted.

“Listen,” Julie reasoned, “you may have been born a boy, and if you want to be a boy or girl when you grow up doesn’t matter right now. We’ll worry about that when the time comes. For now, you’re a girl, you should be proud of that. You should say that. Say, ‘I’m a girl and I’m proud of it!’ I know I’m a girl and I’m proud of it, how about you?”

“I’m, I’m… I’m a girl and I’m proud of it,” Kevin said quietly.

“Do girls wear dresses?” Julie asked. “And panties under them?”

“Yes,” Kevin admitted.

“Are you wearing panties and a dress?”

“Yes,” Kevin answered.

“Why are you wearing them? Are you a boy?” Kevin wasn’t sure how to answer that question. He knew what was hidden in his panties, and that was almost a shameful secret. Julie sensed his trepidation and answered the question herself. “I don’t see a boy in front of me, I see a beautiful girl, someone who I am proud to call my daughter.”

Kevin just ran over and gave his mother a big hug. For once, it didn’t seem to matter what was in his underwear, he could be the girl that he wanted to see himself become.
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#28
Kevin is very lucky and still has allot to learn, lovely chapter.
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#29
Indeed, getting in touch with his femininity is as much about etiquette and manner as it is the clothing. Kevin is clearly eager to learn though so I am quite sure such things will soon become second nature to him.  Wink
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