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Caught
#11
Beautifully written. Kevin is very lucky.
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#12
Indeed, Kevin is about to start out on what will undoubtedly be a beautiful journey, made all the easier by the input of loving and caring parenting. It was interesting that he didn’t want others to find out. 

I wonder if that is as straightforward as it sounds or whether as we have discussed on here before (and I to great extent have experienced) he is merely concerned with what his associates might think. With such a strong support network, if he really is serious he may well make use of it when it comes to addressing this hurdle.
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#13
Totally agree with Girllygirl on both her points.
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#14
I'm very much enjoying this story
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#15
I was similarly caught once, but unfortunately never got the lovely results Kevin is getting. Of course if I did, I would have been embarrassed if others found out and still would be. Thoroughly enjoying the story.
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#16
Next bit...

“I’m glad you were honest about this,” Julie said as she walked over to Kevin to give him a big hug. “I’m not sure how soon we’ll be able to go get you your own things, but we will. Now, Tim is going to be home pretty soon with your sisters, I’m not sure Lisa would be happy I let you borrow her dress and you may want to wash that makeup off and brush out your hair. They’re probably going to see you dressed up at some point and we’ll make sure they don’t tease you or cause any trouble, but you may not be ready for them to know just yet, so shall we get you changed?”

Kevin agreed, and they headed upstairs where Julie helped him out of the dress and took it back to hang up in Lisa’s closet. Kevin pulled his shorts and t-shirt back on before his mother walked him into the bathroom and helped him wash the pale lipstick and blush off his face and brush the slight curls out of his hair.

“You still have your panties to wear like you want,” Julie assured Kevin, “but it may be next weekend before we can go get you your own things. In the meantime, try to think about what you want with all of this. Do you just want to wear girl’s clothes sometimes? Maybe you feel like you’re a girl instead of a boy? Depending on what you want, there are things that could be done to make your body look like a girl, and I don’t want you to think you have to make up your mind right now, but I want you to think about who you are inside and how you want the world to see you.”

It was less than fifteen minutes later that Tim was back home with the girls. “How did things go today?” he asked Julie as they entered.

“Great,” she said, “we’ll talk more tonight.”

The rest of the day was uneventful. The family did their once weekly night out to eat, and came home to relax. It wasn’t long before the kids were in bed and Julie and Tim had retired to their bedroom as well.

“So,” Tim began, “what happened today?”

“Well, after you guys left,” Julie recounted, “Kevin went to get dressed and I took that opportunity to get out one of Lisa’s dresses. When he came downstairs, I offered to let him wear it if he wanted. Honestly, I kind of wanted to see how he would look as a girl as well. When I got him changed into the dress I noticed he was wearing a pair of his panties, and not only that he had an erection. It seems he certainly liked it!”

Tim chuckled softly. “He said he wanted to wear the dress? Did he say why?”

“He didn’t say why he wanted to wear it, and that’s something he will need to figure out at some point,” Julie responded. “I put a little blush and lipstick on him and did a little bit with his hair and I swear you would not believe he wasn’t a girl.”

“Get any pictures of it?” Tim asked.

“Of course,” Julie replied, “I wanted something to remember it in case he never wanted to do it again.” She grabbed her phone and brought up the photos to show her husband, flipping through them one by one.

“He doesn’t look too happy at first,” Tim noted, “but he certainly seems to be a lot happier in the last pictures.”

“He relaxed after a bit,” she explained, “I think he was worried about being seen as weird or being made fun of. I think once he realized I wasn’t bothered by him dressing like that, things were better.”

“You are right though,” Tim agreed, “I would never know he wasn’t a girl in these pictures.” He handed Julie’s phone back to her. “The question at the end of all this is now what?”

“That was my question to him as well,” Julie answered, “I asked him if he wanted to wear girl’s clothes again, I told him we could buy him his own things if he did.”

“I knew we had agreed on getting him his own panties,” Tim raised an eyebrow, “but I don’t know we had discussed beyond that. You had wanted us out of the house for a while today in case he wanted to try on the dress, I just hadn’t realized you were going to offer buying him more things.”

“I’m sorry, I thought you had figured that was where this might go,” Julie apologized. “I mean, after getting him his own panties and then finding out he wants dresses and skirts as well, he can’t be borrowing his sister’s stuff all the time. We can either support him or make him feel like we don’t love who he is, I figured this was the way we had to go.”

“You’re right,” Tim nodded. “He can’t really be borrowing stuff from the girls all the time, and I want him to know we love him no matter what. Go ahead and get him those clothes.”

“Sorry we hadn’t clarified this between us better,” Julie said. “I spent the last several days researching a lot on this and trying to see where things could go from here. I was a bit preoccupied with it, and it’s going to take a while to help Kevin figure out what he wants with all of it as well. It’s one of those things that it could just be a kink or fetish or he could be transgender.”

“So where do you see things going?” Tim wanted to know.

“Well, for starters, I’m going to go through and get him the clothes I said I would,” Julie proposed. “I figure one or two dresses, maybe a skirt and blouse, and probably a nightie or two. He’ll probably need a few more pairs of panties, and then a pair of shoes to match.”

“How and when are you planning on doing that?” he pressed.

“Well, I really want him with me to try things on to make sure they fit, so it would have to be next weekend,” Julie reasoned. “From there, I know Lisa has another soccer game, but Kristen doesn’t have anything as of yet. I may have to let Kristen know about it, I think it would be best if Kevin went in a dress so nobody thinks he’s a boy getting these things bought for him.”

“Makes sense,” Tim agreed, “Do you think the girls would give him a hard time over it?”

“I don’t think so,” she answered. “They’re pretty open-minded and really seem to care about him. They haven’t said anything about his bedwetting over the years, I’m certain they’ll keep quiet about this as well.”

“Well, let me know if there’s anything you need me to do,” Tim finished.

“For now, just understand what is happening,” Julie went on, “but when the time comes for him to be in front of you as a girl, just let him know it’s OK and you love him.”

“Well, that’s a given.” Julie smiled and kissed Tim before they went to sleep.

I was going to add a bit in here about things Julie learned while doing her research on kinks that could go along with the sissy side of things. From there, explaining them to Tim and finding out that maybe the two of them want to try some of those things in their bedroom, but I didn't want to detract from the focus on Kevin--thoughts??
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#17
Great chapter. Focus on Kevin for now and later a separate story chronicling Julie research for things with Tim in their bedroom.
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#18
It is good to see that Julie has such well thought out ideas; Kevin can rest assured that he will be provided with whatever support and whichever options he feels he needs.
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#19
Next chapter, still more to write...

Little was said over the next week about Kevin’s desire to have his own dresses. On Thursday, Julie went to do the laundry and noted that the panties she had bought for Kevin weren’t in to be washed. When he arrived home from school, she once again talked privately with him, reminding him that if they were going to go shopping for his own things, they would do it with him in a dress so everyone would think he was a girl and that she needed to make sure he had clean underwear.

“Sorry, mom,” Kevin apologized, “I didn’t know how to deal with them and not have everyone else find out.”

“They need washed, just like any other clothes, and at some point your sisters are going to find out,” Julie explained. “Tim already knows and doesn’t have an issue with it.”

“He does?” Kevin looked worried.

“Yes, I showed him the pictures of you from last weekend,” Julie told him. “He said the same thing that I did—you make a very pretty girl. He’s not going to say anything mean to you about it or care about you any less because you wear different clothes.”

“OK,” Kevin relaxed slightly. He went over to his dresser and pulled out all three pairs of panties his mother had originally bought him and gave them to his mother to wash. She grabbed the obviously worn garments and took them to the laundry hamper in the master bedroom. She stopped for a minute, grabbed a measuring tape, and went back to Kevin’s room.

“One more thing,” Julie said, “before we go shopping, I’d like to get a couple measurements to make sure we get the right size for things you might not get to try on. The panties I got you were the same size as Lisa’s, they seemed to fit fine, but I want to make sure we’re getting you the right size and not too big or too small.

“Go ahead and take your shirt and shorts off,” she asked him. He complied and she wrapped the tape around his waist and made a mental note of it. “Raise your arms up,” she instructed and wrapped the tape around his chest and again looked at the measurement. “OK,” she finished, “I think we’re all set for Saturday.”

That night, she and Tim were discussing the plans for the weekend before going to sleep.

“So,” Tim began, “the big shopping trip is coming up, isn’t it?”

“It is,” Julie answered, “though there are still some things I need to figure out.”

“Such as?”

“Well, you’re taking Lisa to her soccer game, right?” Tim nodded as Julie continued. “But Kristen doesn’t have plans so she’s going to find out. Not to mention that Lisa is obviously going to find out at some point as well. I’m wondering if I should talk to them tomorrow so they don’t get a surprise.”

“That may be the best way to go about it,” Tim agreed.

“From there,” Julie continued, “I figure I’ll let Kevin wear the same dress as last weekend so he doesn’t get seen as a boy, especially if I want him to try things on. Other than that, it’s just a question of what to get him.”

“What sort of things were you thinking of getting him?” Tim was curious.

“At least one or two dresses and maybe a skirt or blouse,” Julie said, going through her mental list, “Probably a few more pairs of panties, maybe a training bra or two, some socks or tights, and then definitely some shoes to match. Oh, and I’m thinking of also getting him a nightie and maybe a bathing suit.”

“Training bra?” Tim was surprised. “He’s not going to be developing breasts, is he?”

“Well, that depends,” Julie responded, “if he wants to go that route and ends up on hormones, then yes, he will. Even if he doesn’t, he’s at the age that most girls are getting their first bras, I figured he would want to be dressing like other girls his age.”

“I guess that makes sense,” Tim said.

“I’ve spent a fair bit of time looking into all of this,” Julie reasoned. “The boys who are crossdressers or transgender tend to like dressing just like girls their age. Now, there are some who like to be diapered and play as baby girls, but I don’t think that matches what Kevin wants. He hates that he wets the bed and needs the pullups, so I don’t think he wants to be treated like a baby.”

“You really have done your research, haven’t you?”

“Maybe at some point we’ll talk about the things some of the grown men into this like,” Julie suggested. “Who knows, maybe you’d like something along those lines.”

“I don’t know, I’d have to hear about it,” Tim answered. They finished up their conversation and went to sleep.

The next afternoon, when the children got home from school, Julie decided that she needed to talk to the girls about what was happening with Kevin. She followed Lisa into her room and shut the door before starting.

“Lisa, hun,” she started, “I need to tell you something about your brother. This may be a bit of a shock, but he likes to dress in girl’s clothes.”

“I wondered if he had been in some of my things,” Lisa replied.

“Well, he had and it’s going to stop,” Julie continued. “The reason it’s going to stop is because we’re going to get him his own things to wear. I already bought him some panties of his own, and I borrowed one of your dresses last weekend to put him in for a little while. He really enjoyed it and wants his own things so he can dress up.”

“Wow, OK,” Lisa said. “So what’s the big deal with it all?”

“Well, that’s the thing,” Julie went on, “we don’t want it to be a big deal. At some point your going to see him walking around in a dress and looking like a girl, and we don’t want you to be shocked by it. He’s your brother, and he needs us to love him whether he dresses as a boy or a girl. Other than that, I was wondering if you would allow him to wear the dress again tomorrow, I wanted to take him shopping for his own things and it would be easier if everyone thought he was a girl.”

“Yeah, I guess,” Lisa answered. “You said you put him in one of my dresses last weekend? Is that the same one you want?”

“Yes, that would be nice,” Julie said. “Your yellow one there.” Julie pointed to Lisa’s closet.

“As long as he takes care of it while he’s wearing it,” Lisa asked. “I don’t want him getting it dirty or ruining it.”

“He will take care of it, I will make sure of it,” Julie assured her.

“So I’m going to get to see what he looks like dressed as a girl?” Lisa questioned.

“I’ve got pictures from last weekend, would you like to see those first?” Julie pulled out her phone and brought up the photos. They thumbed through the pictures for a few minutes.

“Wow, mom, he really does look like a girl,” Lisa admitted. “I mean, I can tell it’s him, but if I didn’t know him I would swear he was a girl.”

“See,” Julie said, “he likes it and it seems to make him really happy. So, be nice to him when you see him dressed up.” Lisa agreed and Julie stepped out to talk to her eldest daughter.

Julie stepped in to the other girl’s room and again explained what was happening with Kevin. This time, at least, she didn’t have to explain about Kevin being in her clothes or needing to borrow something to wear the next day. She did, however, warn her that she would be seeing her brother in a dress since she was likely going to be joining them the next day.

“I want you to be nice to him,” Julie made sure. She again pulled out the photos. “He makes a very pretty girl, and I want him to be happy through this.” Kristen agreed that she wouldn’t make fun of him, and couldn’t wait until the following day to see him dressed up.
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#20
I do so hope that they let him be a baby girl as well .
Angel A little bit of hanky panky does you good .  Angel
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