Jason's Story
By Kristine Roland

Chapters 6 - 10. This is the story of Jason, a young boy coming to terms with his transgender nature. Helped by his mostly supportive family.

Chapter 6.

Jason and his family walked into his Aunt Jessica’s home, and found everyone already in the living room.

Jason, his mother and father, all said, “Happy Birthday, Billy!”

Jason’s Mom added, “Four years old today! What a big boy you are getting to be.”

As Jason was making the rounds and saying hello to his Aunts and Uncles, a young girl, about seven came running up to him and shouted, “Jason! Are you going to play with me?”

“Of course I will Emily. But you have to remember that today is Billy’s birthday, not yours, so I have to make plenty of time for him too.”

Jason’s Aunt Sally said to her daughter, “Jason is right Emily, I’m sure you and he will have plenty of time, when Billy takes his nap.”

“That’s ok.”

Billy’s older brother Tom came in and said, “Hey Jason. How’s it going?”

“Fine, Tom. Heard your football team won the championship this year. Congratulations.”

“Yeah, we did. Thanks. How did your team do?”

“I really don’t care much for football; I played soccer instead, we finished third.”

“Whatever,” Tom said with obvious disdain, and then added, “well, see ya, I’m going up to my room to play some X-box.”

Jason frowned for a moment, then put on a smile and turned back to Billy and Emily. “So what would you two like to do? Billy, it’s your birthday, so you choose.”

“Wanna play with cars.”

“That sounds like fun. Emily, do you want to join us?”

“Ok.”

Jason took Emily and Billy by the hand and went with them into the playroom in the basement. There he found Billy’s collection of toy cars. He got the box down off the shelf.

Billy, Emily and Jason proceeded to play with the tiny cars for about an hour or so. Billy was starting to get glassy eyed, when his mother came in to get him.

Aunt Jessica said, “Billy, it is time for you to take a nap.”

“Don’t wanna!”

“Billy, you do what your mother tells you to do, or I won’t be able to play with you any more!”

“Oh, ok.” Billy said with a pout on his face.

“Thanks Jason,” his Aunt Jessica said with a smile.

“No problem, Aunt Jessica.”

“So Emily, what would you like to do now?”

“We could play with my Dolly?”

“If you like.” Jason settled down with Emily and followed her lead, playing with her.

A little while later, Tom came into the room.

“Dolls, Jason? You don’t like football, and you play with dolls. Sheesh.”

“What’s your problem Tom? I’m just being a good cousin.”

“Boys don’t play with dolls.”

“Tom, don’t be an idiot,” Jason replied. “Emily doesn’t have anyone else to play with, and this is what she wants to do. I played cars with Billy because that is what he wanted to do.”

“Whatever.” Tom sneered back at him.

“Why shouldn’t Jason play dolls with me,” asked Emily?

“Because dolls are for girls. Boys don’t play with dolls!” Tom said.

Emily looked puzzled, “What do you mean, my friend Christopher plays with his He-man and GI-Joe dolls, and he is a boy.”

“Those aren’t dolls, they are action figures,” said Tom. “It’s not the same. He probably stages battles and fights wars with them; he doesn’t have tea parties and play dress up with them.”

“Yes he does, he is always changing his uniform, and his accessories. How is that any different?” Emily was completely confused.

“It just is. I’m sure he would not want to play with your dolls.” Tom said.

“Tom you are being ridiculous. I’ve seen Emily and Christopher play, and they set up elaborate plots. GI Joe sometimes does sit down with Barbie and have tea, but then they go off and get involved in some international intrigue. Emily’s Barbie could give James Bond a run for his money.”

“I’m sure.”

“Was there something you wanted when you came in here Tom, or did you just come to be a pain in the butt?” asked Jason.

“I’m just getting my baseball glove; I’m going to hang out with some friends.” Tom got his glove and left.

“Why is he such a jerk?” Emily asked.

“I don’t know Emily, don’t worry about Tom. He doesn’t know what he is talking about.” Jason replied. “Forget him; let’s get back to our game.”

The rest of the afternoon passed without incident. After dinner, cake and the opening of Billy’s presents, Kristine said, “Ok, Jason it is time to head home.” Jason nodded, and said goodnight to his Aunt and Uncle, Billy and even Tom.

Richard pulled his sister Sally aside and asked her, “Do you have to head straight home, or can you come by our house for a bit?”

Sally gave him a bit of a questioning look, but responded, “It’s pretty much on the way, so we could stop by for a little while.”

“Thanks Sally. We will meet you there.” Richard replied.

Chapter 7

Jason was quiet as they got into the car to head home. He was thinking about how Tom had acted earlier today, he knew without question that Tom would never accept him if he found out. Moreover, he knew that Tom’s attitudes were just a reflection of his parents. Knowing that once they find out that he will probably never be able to see Billy again hurt.

“What’s the matter, Jason?” his mother asked.

“I’m just thinking about how sad it is that I may lose touch with Billy. Tom jumped all over me today just for playing with Emily and her dolls. I wasn’t thinking about being a girl, just Emily’s older cousin. I like that Emily and Billy enjoy my company. Is there anything wrong with that?”

“Of course not Jason. It’s true though that most boys your age would rather go out and play with other boys their age, then hang out with their younger cousins,” his mother said.

“Mom, I like going out and playing ball. And I would have had a good time if I had gone and played with Tom and his pals, but Billy and Emily would have been disappointed, and I would hate to do that to them. I don’t see them every day, I can always go play ball with my friends.” Jason replied.

His mother nodded, “I understand, Jason. But you know that may just be another manifestation of the whole thing. You are much more nurturing then a typical boy your age. That is not a bad thing, in fact it makes you special, and if that is part of what is going on here, I would not want to do anything that would change that part of you.”

“Dad, why did you ask Aunt Sally to stop at our house?”

“Your mother and I talked it over, and we would like to talk to her about you. Sally is very liberal, and she is friends with lots of people that lead ‘alternative’ lifestyles. If things go the way that Dr. Adams thinks they will, then her contacts may be able to assist us. There is no doubt in my mind that she will be very supportive to you, no matter what path turns out to be right for you. I am also confident that she will be discrete for now.”

“Oh. You really think she will accept me?”

“Jason, it will be far easier for her then it is for your mother and me.”

“I’m sorry Dad. I don’t want to be a disappointment to you.” Jason said in a small voice.

“Jason, I keep telling you, you are not a disappointment to me, or your mother. It may not be easy, but you are our son, and we love you, no matter what. It is just going to take some adjustment on our part to fully accept this.”

With that, they pulled into the driveway at Jason’s house, and went inside.

They all headed into the living room. Jason’s mom and Aunt Sally put together a tray of soft drinks and brought them in.

Sally said, “Ok, Richard what did you want to talk about?”

Richard looked at Jason and Emily. “Emily, I need to talk to your mom for a little bit about a private matter, but I need Jason to be a part of it. Can you go play in the rec room for a while on your own? Jason will be in, in a little bit.”

“Ok, I guess, Uncle Richard.”

“Jason, take her in, and come on back please.”

Sally raised her eyebrow, but did not say anything. A few minutes later, Jason returned.

“So, what is this about, Richard?” Sally asked?

“Jason recently admitted to us that he is transgender. We are not really certain yet as to whether he is a cross-dresser or a Trans-sexual. He actually is going to be seeing a psychologist starting on Wednesday. Knowing some of your friends, I was wondering if you had any advice you might be able to give us.”

“Well, that is a bit of a surprise. Jason, come here.”

Jason walked over to his Aunt. Sally reached out and gave him a great big hug. “I want you to know right now that no matter what happens, I love you. You will get nothing but love and affection from Emily and I.”

“Thanks, Aunt Sally. I really appreciate that.”

“Jason, I’m not going to lie to you, it is not an easy life. Depending on just how far you need to take this, it can be very difficult. You have the advantage that your parents will love you whatever happens. Many young people in your position are not so lucky. Can you imagine what would happen if Tom told his parents such a thing?” she asked?

“Yes, I can imagine it. I think about how they are going to react to me, which would be a drop in the bucket to what they would do to Tom.” He said.

“Well, lets hope Tom is not harboring any secrets. Or if he does that he has the sense to keep them secrets for now.” She said. “But enough about Tom. If he is transgender is he is certainly doing his best to over compensate. Emily told me about the way he went after you today. That boy is going to be a problem soon. His father has pushed those ideas on him, and Jessica has bought into it all.”

“In any case, Richard, to answer your question, I do have some contacts, but I think that it is best for you to start out with the psychologist. Assuming of course that you have one that is truly knowledgeable about Transgender issues. If he starts talking to you about treatments to ‘cure him’, before he really, really gets to know Jason, run, don’t walk away. Now, I’m not saying that there is no chance that Jason can work through this and get beyond this. But in my experience, limited as it is, most of the time, suppressing the need leads to depression and worse.”

“Dr. Adams, Jason’s pediatrician, said that Dr. Daniels is highly respected in the area of Transgender problems.” Richard told her.

“Dr. Daniels? Dr. William Daniels?” she asked.

“Yes, I think that is his name.” Kristine answered.

“Jason’s in good hands then. I’ve never met him, but I know of him. Definitely work with Dr. Daniels first. Once we know more of what Jason is dealing with I can introduce him to the right people.” Sally said.

“Thank you Sally,” both Richard and Kristine replied. Jason gave her a hug and said, “Thanks Aunt Sally, it is nice to know that I have your support too. Now, Dad, can I go back to Emily, I don’t want her feelings to be hurt.”

“Run along.”

Chapter 8

“So Jason, can you tell me when you first started wearing your mother’s clothes?” Doctor Daniels asked.

“I don’t remember exactly, but I was probably 4 or 5. Mom was not home, my Grandmother was watching me. I remember seeing a bra in the hamper in the bathroom and reaching out to touch it, and trying to figure out how to put it on.” Jason replied.

“And then what?”

“I don’t really remember too much after that, and I don’t remember doing it too many other times after that until a couple of years ago.” Jason answered.

“What happened then?”

“Well, Mom had to run an errand, and I was watching a show, she let me stay at home. When she was gone, I started to feel a strong need to try on a bra again. It had been quite a long time, but I was remembering what it had felt like, and I just needed to do it. I went into the hamper and found some panties and a bra, and put them on. I could not believe how good it felt.”

Dr. Daniels asked, “In what way?”

“I felt, I don’t know, relaxed, but also excited, and well… aroused. And then I felt a little guilty because I felt aroused, but I just could not stop.”

“What did you find arousing?”

“I’m not sure. I was thinking about breasts filling out the bra, and other things in the panties.”

“Your mother’s breasts and vagina?”

“No... I mean sure, I knew these were hers, but I was not thinking about that, I was thinking of my own, or some of the girls at school.”

“Did you masturbate?”

“Not intentionally, I really had not done that before, but basically I did, without realizing it.”

“What happened then?”

“I felt really, really guilty. I did not really know what I had done, but I was sure I should not have done it. I took everything off, cleaned up as best I could and put everything back in the hamper. Then I swore I would never, ever do anything so stupid again.”

“How long did that last?”

“A few weeks, but then I just could not help myself, and found myself doing it again. Eventually I got brave enough to even go into Mom’s drawers when there was nothing in the hamper. But I love my parents and I hated lying to them, and I hated stealing from my Mom. I finally took a bra and panty and kept it, and then I just felt awful with the guilt from that, till I finally had to tell Mom, a few weeks ago.”

“How did she handle being told this?”

“Well she was concerned, but she did not punish me. She and my dad took me to see Dr. Adams. We had a good talk about it, and he suggested that I come speak to you, to learn more about myself.”

“I’m glad that you and your parents have a strong relationship. That will be very helpful for you.”

“I asked Dr. Adams if you would be able to cure me, and he said he was not sure whether that was the right thing for me or not. What do you think?” Jason asked?

Dr. Daniels put his hands together and replied “Jason, it is too soon to tell what the correct path for you will be. I think the word cure is wrong, because I don’t think that you are sick. What I am going to try to do is work with you to help you to decide what is right. Now let me ask you another question. Are you only interested in wearing girl’s clothes when you masturbate, or do you want to wear them when you are not aroused?”

“Doctor Daniels, if I could throw away all of my boys clothes and start wearing only girls clothes, I would do it in a heartbeat. Pretty much the only time I could do it before was when I could sneak them, and I would get excited, and have to do that. But last Saturday, I told my Mom that I could not take it anymore, and she gave me permission to get dressed. I felt so relaxed, and I did not get aroused. I helped Mom with the cleaning and spent the morning just helping out. It was great.”

Dr. Daniels asked many more questions and Jason answered as best he could. Towards the end of the session, the doctor asked Jason to wait in the waiting room while he spoke with his parents.

“Jason is a very nice, well mannered young man. You should be proud of him. I know that you are concerned about his cross-dressing, as well you should be. But it is clear that you have a strong family, and you will all come through this just fine. It is too early for me to give you a diagnosis. However, here are some observations.”

Jason’s mother and father, nodded their understanding, and waited for the doctor to continue.

“First, Jason began cross-dressing in earnest as puberty started to kick in. He had done it occasionally as a younger child, but it got tied with his earliest self exploration of masturbation, as such it has the risk of becoming a quite strong fetish for him. However it is more than that. Jason told me about his spending the morning with you on Saturday, dressed, which was completely non-sexual. I think that is actually good for him at this point. We want to disassociate the cross-dressing with sexual response. Before now, you combined the imagery of the appropriate body parts, and the thrill of taboo, and risk of getting caught, and that is quite a powerful thing to a 12-14 year old. By making dressing non-taboo, and just clothes, the link to sex will go away. Then from there we can determine if Jason really wants to be a girl, or just to dress like one once in a while. He may even get to be bored with it, and move on, although I must caution you, that it is rare.”

Jason’s mother asks, “So you want me to encourage him to dress?”

“Not necessarily encourage, but certainly don’t discourage it. There needs to be guidelines as to when, but I think that having him help you Saturday mornings is probably a good start. You could also have him help you in the evenings. You want to normalize the behavior, don’t force him, but I really don’t think you will have to twist his arm, at least at first. Later on, he may get tired of it, he may not, but we will have to play that by ear, and I will keep seeing him.”

“How far do we go with this? Just the underwear or full outfits? What about makeup and the rest? And do I make him change into boys clothes for bed?”

“I would start somewhat small, but certainly the underwear, and yes I would buy him a couple of outfits suitable for working around the house. No, if he wants to sleep in his girls clothes, let him, get him a basic nightgown. Don’t make it taboo. He will certainly still masturbate with them, but if it is not taboo, he will fairly quickly stop focusing on the clothes, and concentrate more on whomever he is currently finding arousing.”

“Make sure that when he is dressed as a girl, that he gets treated like a girl. He needs to understand that being a girl is more than just getting to wear different clothing. That girls are treated differently and have different expectations put upon them. Can you do this? Both of you?” Dr. Daniels asked.

Kristine looked at Richard, and he said, “Doctor, I love my son. I don’t understand this at all, but I will love him and support him no matter what. But I have to play devil’s advocate here. If we do this, are we not pretty much making the decision that Jason is never going to move past this? He is going to get so comfortable with it that it will just be what he wears? And then what, how is he ever going to find someone to spend his life with. That is what Kristine and I are afraid of. And what if he decides he wants to go all the way and have surgery?”

“Richard, it is much too soon to worry about surgery. So far, Jason strikes me as much more likely to be a cross-dresser then a trans-sexual, but again it is too soon to tell. If Jason gets that comfortable, then frankly in my experience he was never going to move past it. If you force Jason to ‘quit,’ he will continue to find ways to sneak around. And he will feel terribly guilty about it, as he has already shown. That cannot lead to anything good, believe me I have seen enough of that, and you do not want that for Jason. The other possibility is that once the ‘thrill’ goes out of it that he will move on. I can’t tell you which is going to happen yet, but in my opinion this is the best thing you can do for Jason.”

Kristine takes Richards’s hand, “Honey, I think that it is worth a try. I don’t want Jason to have to feel guilty. Maybe he will get tired of it, but if not, then we will take it from there. Doctor. Thank you.”

“You’re welcome, Mrs. Anderson. I’d like to see Jason every Wednesday for the next few months, until we see how this is working. Same time next week?”

“That will be fine Doctor.” Kristine replied.

“Then I will see him next week, good night.”

“Good night.”

Chapter 9

The ride home that night was quiet. It was kind of late, so the Anderson’s stopped for a quick dinner at a local diner. They discussed school, the upcoming baseball season and basically avoided the topic of what was discussed during Jason’s session with Dr. Daniels.

When they got home, it was time for Jason to get ready for bed. He gave his Mom and Dad a kiss and a hug goodnight, and went off to bed.

Richard and Kristine went to their own room and closed the door, and turned on the TV to make sure that it would be difficult for Jason to over hear their conversation.

“So Richard, are you going to be ok with this?” Kristine asked.

“I meant what I said to Dr. Daniels, Kris, you know that.” he replied.

“I know, Rich, but seeing him dressed up at night. Saturdays are not such a problem for you since you are working most of the time, but you won’t be able to avoid it if we allow it during the week.”

“It will take some getting used to hon, but I can handle it. How about you? You told me it was really, really hard on Saturday.”

“Yes, it was, particularly at first. Of course, I split up our work so we would be in different rooms, which gave me some time to get myself together, but I have to admit, he just looked so much more at peace when he came in to the kitchen, that I could not have done anything else.” She admitted, and then went on, “he is going to want a skirt. Even though it is just for hanging around the house, and most girls his age would just wear jeans, sweats or shorts, he will want a skirt. That is going to be a little bit hard and to see him with ‘sock’ breasts, oh my… If we are going to do this, we really will need to do something better than that.”

Richard replied, “I would say we start off slow, pick him up a couple of outfits, including some girls blouses, and proper clothing for around the house, and get him one ‘nice’ outfit he can wear here for Saturday and Sunday night dinner. Enough underwear for a week, or perhaps two weeks, so that it does not have to be washed every day, and as Dr. Daniels said a basic night gown, and he will need to have a bath robe. If I’m supposed to treat him like a girl, then he should not be running from the shower to his room in underwear anymore.”

“That makes sense. Should I just go buy them, or should I take him with me?” She asked.

Richard thought for a moment and replied, “I think he should go with you. He won’t be able to try things on, because there is no way anyone will believe he is a girl, but he should have some say in what you get, within reason of course.”

“All right then, I will take him out tomorrow after school. Are you going to call Sally and let her know what Dr. Daniels said, or do you want me to talk to her. You know she is probably going crazy wondering how it went.”

“I will call her in the morning on my way into work, it’s a bit late for tonight, you know that Emily wakes up when the phone rings, so I’m sure she won’t be expecting to hear from us tonight.”

“Ok, thanks. We should probably think about having her and Emily over for dinner soon. I don’t think that Emily will have any problem with Jason being dressed as a girl, although Sally will have to make sure she understands that it is something that is a secret for now. See what she thinks. I would say not until after this weekend though, let’s at least get through the first one ourselves before we have Sally and Emily involved. Also for now, Jason will have to understand that he is only to dress at home and when we do not have company, I am not ready to deal with Jessica and Bob finding out.”

“Agreed.”

Chapter 10

When Jason got home from school the next day, his mother was waiting for him in the kitchen. She asked him to sit with her. After the normal questions about his day, and how much homework he had tonight, she told him that she wanted to discuss what she and Jason’s father had decided, based on their discussion with Dr. Daniels the night before.

“We are going to make some changes, to accommodate your needs, and we are going to try some things out. First off, we do not want you to ever feel you need to hide this part of yourself from us again, we don’t think it is good for you to have to sneak around and lie and steal, and we believe that forcing you to quit would be forcing you to do so. So, from this point forward, the restriction on you dressing is lifted, within certain boundaries. First, you are only to dress in this house, and only when we do not have company. We may relax that to not include Aunt Sally and Emily, but we have to discuss that with her first. While we know Sally is supportive, she may not be ready to have Emily know about it yet, since Emily would have to be asked to keep it a secret. That may be too much to ask of Emily, and we will let Aunt Sally make that decision. Do you have any problems with these restrictions?” His mother asked.

“No, not at all,” Jason replied, trying to restrain his excitement.

“Good, I did not think you would object to them. When you are dressed like a girl, we will be treating you like a girl. You can’t have it both ways. You need to understand that being a girl is not all about wearing pretty clothes, etc. There is much more to it, and society treats girls differently from boys. When you come home from school, I will expect you to help out with getting dinner ready; you need to learn to cook. This is not that much different, since you sometimes helped before, as neither your father or I are particularly hung up on the standard gender roles in that way anyway, but more will be expected of you as a girl, then as a boy. Again, you and your father usually helped with the cleanup already as well, so that is not a big change. On the weekends, we will have to see what we can do, since you are supposed to cut the grass, but you can’t go outside dressed, and it still needs to be done, and girls can cut the grass just as well as boys can. On the other hand, I want you to help me out in the house like you did this past week, so we may have to find an alternative way of getting the lawn done.”

“Not a problem, I can do it, and then come in and help you.”

“Jason, you will still be in baseball, and any of the other activities that you enjoy. You will have to be on the boys teams of course, and I don’t want you to give up your friends for this. But there will be plenty of time for you to spend dressed. You know, if you are going to be treated like a girl when you are dressed, we really will need to come up with a name for you, since Jason will hardly fit. Do you have one that you think you would like?”

Jason thought for a moment and said, “I always liked the name Kelly.”

“Kelly it is then. Ok, Kelly, we are going to need to get you some more clothes. A bra and a panty are not going to cut it, if you are going to be helping me out every evening, and on the weekends. So, I’m going to need to take some measurements, please go get changed, and put on your panty and bra, and nothing else, and I will be in, in just a moment. I need to go fetch the tape measure. Oh, please make sure you use your padding, I’m afraid you still need a little help in the chest area my dear.”

Jason practically jumped out of his chair and headed into his room. “Oh… My... God…” he thought. “I cannot believe this is really happening to me. Mom is taking me shopping for girl’s clothes, for me!” Jason went straight to his dresser drawer, took out his bra and panty, and got out of his boy clothes as quickly as he could. He pulled up the panty, and put on the bra, and grabbed some socks and filled the cups as best he could. A moment later, his mother knocked on the door.

Jason was suddenly embarrassed as he realized he was going to be standing in front of her with nothing on but a bra and panties, but he opened the door and let her in. Kristine noticed that Jason was blushing, and he was trying to cover up both his crotch area and, to her amusement, his chest.

“Now Kelly, there is no reason for you to be embarrassed. I have seen you naked since the day you were born, and you have never been worried about me seeing you in your underwear before, so there is no reason for you to start now. Although, you will have to be careful about letting your father see you in your underwear now. It is just not the same for a father and a daughter as it is for a mother and a son. Chalk that up as one of the first differences you will have to learn.”

“Now unfortunately Kelly, at least at this point there is no way that anyone is going to think that you are a girl. In time, we may be able to help you with that, but puberty is certainly not helping you there. I’m afraid you are going to be dealing with some body hair issues fairly soon, as you are showing all the signs that you will be following in your father’s footsteps. For now, we are not going to worry about it, as you will only be Kelly here with your father and I, and maybe Aunt Sally and Emily. If after some time, we all feel that you need to go further down the line toward becoming a girl we can start to look into how to hide the masculine features and emphasize the feminine. But that is something to worry about in the future, after we have a better idea of what you need. OK?”

“Ok, Mom.” Jason replied his expression and tone a little deflated.

“Kelly, don’t let this get you down, your father and I, and your Aunt Sally are all definitely here for you, and we are going to make this work out, one way or the other for you. If you are going to do this, we need to start somewhere. Now the only reason I even mentioned it is because, we are not going to be able to go and try things on at the store. That would be a little difficult to explain. So we need to take really good measurements so that what we buy will fit. This is especially true for the underwear, because we can’t take it back, once it has been opened. Ok.”

“Ok” Jason replied with more enthusiasm.

Kristine took all of the measurements, and wrote them down, and then said, “Ok, Kelly, I’m afraid you have to take off the bra. But I’ll tell you what, leave on the panties, just this once. No one is going to see them through your jeans. Just be glad you don’t wear them down around your butt, like some of your peers do, as that would not work. Make it quick, so we can get moving.”

Jason probably never got dressed so quickly in his life.

“Kelly, I’m sure that you have had fantasies about going shopping for a complete new wardrobe, but I want you to understand that we are not going to go hog wild today. We are going to start by picking up several packets of sensible panties, a couple of bras, a couple of around the house outfits, and one nice outfit for Saturday and Sunday dinners. And of course any basic extras needed to complete the outfit, like hose, trouser socks, and a pair of nice shoes, and around the house shoes. You will probably need a slip too, since I’m assuming you are going to insist that the nice outfit be a dress. But we are not going to go crazy, and we are not going to do any makeup or jewelry for the moment. Understand?”

“Yes Mom, I do.” Jason replied. He knew his mom thought that he might be disappointed, but quite the contrary, as he heard her list of what they would be looking for, Jason thought he would burst with joy. “Oh… God… a COUPLE of bras, and several packets of panties! A nice DRESS, and a slip... and everything! OhMyGod, OhMyGod, do not let me wake up and find this was all a dream!”

Soon they pulled into the local mall, and after parking headed into the slightly upscale department store that Jason’s mother usually shopped at. They headed to the lingerie department first. Jason had really only seen his mothers panties, so he was shocked to learn that there were so many more styles available. His mother told him that she was not about to buy him thongs, and she suspected they would be quite uncomfortable for Jason anyway, and she likewise thought that the bikini styles were probably risky for Jason at least at the start. She let Jason chose between cotton and nylon, and between full briefs and hi-cut briefs. Jason’s mom typically wore nylon full coverage briefs, so Jason knew he liked the feel of the nylon, so he chose nylon, but he thought the hi-cut briefs were more feminine, so he chose that style. Kristine picked up several packages with a variety of colors and patterns, in his size.

Then she said quietly to him, “Kelly, as you can see, there are literally dozens of styles of bras, and different styles for different needs, etc. We really don’t have time to go through them all here tonight, so since you seem to like the style I have been using, I am going to suggest we just pick up a couple more of those that actually fit you. Mine are a little bit small for you, as your band width is actually a bit bigger than mine. From now on you really need to leave mine alone because you will stretch mine out and I will not be able to wear them. Ok.”

“No problem, Mom. I won’t need to do that anymore.”

“Good.” Kristine went over and picked up two basic white bras in Jason’s size, well Jason’s size with socks anyway she thought. As she thought about that, she looked around, and saw what she was looking for. She found some gel shaping pads, and picked them up. She told Jason that this would work better then socks. She said, “I’ll bet there are a number of girls in your school that are using a bit of ‘help’ too.”

Next they picked out a printed sleep shirt, with a v-neckline with a pretty pink bow, yellow with cute pink polka dots. Then they found a super soft, luxurious bath-robe, it was short and came to about knee length.

Kristine paid for the purchases, and then they headed over to the juniors section.

Here they started to look in earnest for some outfits for Kelly. There were a number of sales people around, so she said perhaps a little loudly, “Jason, you know Kelly better than I do, I need you to help me to pick out some things that she will like.”

Jason was quick on the uptake and responded, “I’ll do my best Mom; I don’t know much about girl’s clothes though.” Kristine smiled, “I know Jason, but you know what she wears, so just try to imagine her in what you see, and think if it seems to be similar to what she would chose for herself.”

“Ok Mom, I’ll do that.” He smiled back at her.

Jason thought about a girl in his school that he really liked, and who he thought was very pretty. He tried to think about what she would wear, and used that to guide him as he worked through the department with his mother. His mother told him that they were looking for a couple of nice tops, and some comfortable slacks or shorts for around the house. Kristine was pleasantly surprised as they went through and looked, to discover that Jason actually had fairly good taste. In the end they chose a nice, white short sleeved peasant top, it had a tie-neck with a keyhole front, and was shirred at the hem with a simple ruffle. Then they picked out a couple of basic beaded, scoop necked tees in a ribbed cotton, since they were buy one get one. They got one in tropical pink and another in a light green.

They picked out a pair of black cropped leggings, and a pair of basic white stretch Capri pants. Then Jason saw, a pleated denim skirt, knee length, with an A-line shape, and he just had to have it. Kristine knew she was not going to get away without picking up a skirt, so she let Jason get that as well.

Then they went to look at the dresses, so that he would have a nice weekend meal outfit. They found a pretty navy sheath dress that came to the knee. After paying for the outfits, they headed back over to the lingerie department and picked up a slip, and knee highs, trouser socks and panty hose to go with the various outfits they had picked up. Then they headed out into the mall to the one of the self service shoe stores.

“Ok, Jason, this is going to be the tough part, because we really cannot buy shoes without trying them on. So we are going to have to find something here. Come on back towards the back of the store.” She led Jason to a set of chairs out of sight from the entrance way, and had him sit down. “Wait here.” She told him. A few moments later she came back with a pair of nylon footies and a women’s shoe sizing tool. “Here, take off your shoes and your socks and put these on.”

“What are these?” Jason asked.

“They are footies. Your socks are too thick, most women’s shoes, except sneakers of course, are designed to be worn with nylons, bare feet, or thin ‘trouser’ socks. You can’t try on shoes with bare feet, so shoe stores keep these ‘footies’ to allow women to try on shoes. Here is a pair of boys’ shoes, so that it looks like you are trying them. Ok, now let me measure you.”

After taking the measurements, she went and grabbed a pair of simple slip on flats and a very basic pump with a minimal heel.

“Jason, again, there are tons of styles, but we don’t have time for me to teach that to you tonight. These are pretty basic shoes to start you out with, and will work for the outfits you have right now. Try them on quickly. Fortunately the store is pretty empty. I’m sure that there is probably a surveillance camera, but that can’t be helped.”

Jason quickly tried on both pairs, and they seemed to fit fine. When he stood on the pumps, even with the low heel it felt very strange, but he knew it was something he would have to get used to, if he was going to dress as Kelly.

His mom was satisfied that they would work so she told Jason to go ahead, and that he should go wait for him in one of the sitting areas by the mall entrance.

Jason went and found a seat, and started to think about all that they had done this evening. He was hard pressed to keep from going into the bags, and reviewing, but he knew how that would look, so he avoided it.

While he was waiting, a group of girls from his school walked by. “Hi Jason, what are you doing?”

“Hi Julie, Kathy, Sue. Nothing much, just waiting for my Mom. She had some shopping to do, and needed some help carrying things. She is just paying for the last of it, and so she let me come out here to take a load off. How about you?”

“Oh we are just hanging out, you know us girls; love to go to the mall. My Mom is supposed to be here any minute to pick us up. Mind if we sit here with you while we wait?”

“No, of course not. Here let me make some more room for you.”

“Looks like your Mom was busy, I love that store. What was she getting?”

“Oh, just some clothes.”

“Did you get anything nice?”

“What do you mean?” Jason asked startled.

“Well they have some really nice clothes for boys in there too. I figured since you were here with her, you might have gotten something too.”

“Um, no, most of this is for my cousin Kelly. Her birthday is coming up.” Jason improvised.

“Oh, how old is she?” Julie asked.

“Um… She is our age.” Jason replied.

“Can we see? You know Mom’s are out of touch, maybe we can help make sure that Kelly is going to like her presents.”

“Um… I don’t know, I don’t want to mess anything up, and Mom will be here in just a second.” Jason stalled.

“Oh, we would not mess anything up silly, we do this kind of thing all the time, right girls.” Kathy and Sue both agreed. Jason was not sure what to do, but fortunately he heard his mother say from behind him, “Do what kind of thing all the time? Hi Jason; who are all of your friends?”

“Hello Mrs. Anderson. I’m Julie, and this is Kathy and Sue. We go to school with Jason, and he was just telling us that he came here today to help you carry around the stuff you bought for his cousin Kelly. We were offering to take a look at what you got her to make sure that a girl our age would like it.” As Kristine raised her eyebrows, Julie quickly added, “Oh, I did not mean to be offensive, Mrs. Anderson, but you know our Mom’s have decidedly different tastes then we do, and since you don’t have a teenage daughter, well…” Julie was embarrassed. “Oh, my, really I’m sorry, that sounds horrible when I hear myself say it, but really I was not trying to be.”

Kristine laughed, “Julie, it is a pleasure to meet you. Kathy, Sue you too. I understand what you mean Julie, believe me, I had the same problem with my mother when I was your age.”

“I’ll tell you what, I will satisfy your curiosity, but let me open the bags, because frankly, I also picked up some unmentionables, and I don’t particularly want to be parading them out in the mall lobby.”

The girls laughed, and Jason blushed.

“Jason hand me that bag, the big one that has the gifts for Kelly.” Jason handed the bag over, and Kristine pulled out the capri’s and the leggings first. The girls acknowledged that while not overly exciting, they were basic pieces that would certainly be welcome. Then came the peasant top, which the girls liked a lot better, and they thought that the two tees were cute. They loved the denim skirt, in fact Kathy asked how much it was, and when she heard the answer, she said, “Oooh, did they have more?” When Kristine told her yes, she said “I have got to go get one of those.” They also liked the navy dress.

Julie said, “Mrs. Anderson, you have fine tastes.”

“Thank you Julie.”

Kathy said, “Julie, I’m going to run over there quick, I’ll be right back, I love that skirt.”

“Ok, but hurry, Mom will be here any minute, and she will not be happy if she has to wait for you!”

“Ok,” and Kathy hurried over to the store.

“She will never get back here in time,” Julie said. “She will see 5 other things, and have to try them on and oh… Mom is going to be annoyed.”

“Is you’re Mom going to be coming in, or are you supposed to meet her outside?” Kristine asked.

“She will park and come in; she does not like us to wait outside, because all of the smokers hang by the door. She does not want us to have to breathe all of that smoke.” Julie replied.

“Well, Jason and I can wait here with you and I can try to distract her, while you go fetch Kathy, if necessary.”

“Really, that would be great. Jason, your mother is cool.”

“Thanks, Julie, I think so too.” Jason replied in all honesty.

A few minutes later, Julie’s mother came in the mall entrance, and came over to greet her daughter. “Where is Kathy?” she asked as she rolled her eyes.

Julie replied quickly, “She just ran back for a minute, let me go get her.”

“Make it quick, Julie!”

“Ok Mom, by the way this is Mrs. Anderson, and Jason. Jason is in my class.” Julie said and then rushed off to get Kathy.

“Hello Mrs. Anderson and Jason.”

“Hi, and its Kristine, I’m afraid, Julie forgot to tell me your name.”

“Oh, I’m sorry; I’m Shelly, Shelly Sanders.”

“I’m afraid the delay is my fault. The girls were critiquing my choices for gifts for my niece, Kelly. Kelly is the same age as this crew here, so they thought they should make sure I was not getting her old lady clothes. Not that they put it that way… Sue don’t worry, I really thought it was funny. Anyway, Kathy saw the skirt I bought Kelly and had to go get one herself.”

“That sounds like Kathy. Jason came along with you to shop for his cousin?”

“Yes, I needed help with the bags, and actually Jason was a lot of help, keeping me on track with what he has seen the girls his age wear.” Kristine replied.

“That was very helpful of you Jason. I wish my son were as helpful. He is a year younger then Julie, and there is no way I would bring him along, because I would spend the whole time yelling at him. Of course if I brought Julie, it would cost me three times as much, as she would see so many things she would just have to have!”

Kristine laughed. Julie and Kathy came running back, Kathy with a new bag in her hands. “Thanks Mrs. Anderson, I got it. Sorry Mrs. Sanders, I did not mean to hold you up.”

“Oh, alright Kathy, but next time… Anyway, get your stuff, I have to get you all home, and get dinner ready. Nice to meet you Mrs. Anderson, Jason.”

“See you at school tomorrow Jason.” Julie said to Jason. Jason replied, “Good night, see you tomorrow.”

After they had gone, Kristine said to Jason, “Ok Kelly, grab your bags, and let’s go home.”

Jason picked up the bags, and walked with his mother out of the mall.