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Training Bra Entry
#11
(03-12-2018, 07:37 AM)sgbf Wrote: You're just in time for supper, Jack. How was your time after school at Donna's?

Hi Mom. It was fine. We finished our homework project and then played some video games.

That's nice dear. It is nice that you teamed up with her on your school project. She is one of the brightest students in your grade.

Yeah. I think I only beat her score on maybe two or three things the whole year. She always makes it fun to compete with her, teasing me when she does better, but always very supportive the times that I get a higher mark than her. I like her attitude.

Well she does seem like a very nice girl. Her mother is always cheerful, wherever I have seen her.

Donna was really excited today. Her mother took her out last weekend to shop for her first bras. I thought that most girls would be pretty private about the whole thing. But Donna is always so open about things. She was happy and thrilled and couldn't help but share her excitement with me.

Well it is a pretty special time for a girl, when she is ready to start wearing a bra for the first time. She is on the verge of being a grown woman. It is nice that she feels close to you and comfortable enough to show her excitement to you.

That's not the only thing she showed me. She took the two other bras out of her dresser to show them to me. She said that boys can sometimes be jerks, snapping girl's bra straps and teasing girls about their bras and she thinks it is simply because boys are curious about them and they never get the chance to really see what they are all about.

That's very forthcoming of her. Usually girls want to keep their underwear hidden from boys.

She did, Mom. I only saw the bras that she was not wearing.

Oh, I see. So then what did you think of them?

Well Donna showed me how it attaches in the back, and how the straps adjust and how the light padding in the front, even though it is pretty thin, can still make things smooth. Mom, I hope that you won't be mad, but I got swept along in all of Donna's excitement and when she wanted to show me how good the strap adjustments are to keep them from falling down and that this could only be demonstrated over a pair of real shoulders, well….

Well what dear?

Well, I hope that you won't be mad, but she helped me to put it on so she could show me how it all adjusts. I didn't have the bra on for very long, just so I could understand how it all worked. That way, she said, I would never have to act like a jerk, since I would already know all about how bras work.

That sounds quite logical. So do you now feel you are educated about girl's bras?

Well I certainly know more about them than I ever thought I would. I know what it feels like to wear one, even if it was only for a few minutes.

And how did it feel to you, Jack?

Well, it was weird having the band around my chest hugging me all the time regardless of any movement that I would make. And I could move my arms and shoulders up and down and the straps wouldn't budge holding the cups in place all the time. It was a strange feeling, but not uncomfortable.

Well Jack, bra straps are not uncomfortable when there is no weight to hold up. But if the straps are not wide enough, and the size of the breasts that they are holding up are heavy enough, then the pressure of the strap eating into your shoulders can be uncomfortable after wearing it for a whole day.

Yeah I suppose it could be.

Well that was very kind of Donna, to give you an education on girl's bras to keep you from acting like a jerk later on.

Yeah, well I'm just glad that I don't have to wear one all the time. 

*** –

Um, Mom?

Yes Jack, what is it?

You know that for my birthday I asked you for that video game and a new baseball mitt? 

I remember, dear.

Well I was wondering if I might be able to ask for one more thing.

What's that Jack?

I know this is going to sound strange, Mom. But I can't stop thinking about how Donna's bra felt when I tried it on. Do you think it would be ok for you to buy a bra for me, so I can wear it at home from time to time? I know boys don't need to wear bras, and shouldn't do that in public, or they would probably get beat up. It's just, I don't know, I'm still curious about how it might feel to wear it for a longer time. Is that too strange, Mom?

Well Jack, I don't know what to say. I never expected that my son would ask me for a birthday gift of a girl's bra. Do you want to become a girl? Do you like being a boy?

Mom! Of course I like being a boy and no I don't want to become a girl. I am happy being a boy. It's just. Well, I am curious about girls and girl's things. Girls are often nicer than boys, and well, they can look so pretty sometimes. They look and smell and feel nice, not like boys do. I just wonder what it would be like, having a bra hug me for a long time, and feel the straps over my shoulders too. You didn't get mad at me when I told you about the time I tried on Donna's bra, so I thought that it might be ok.

Hmmm, Jack. Let me think about it ok? I'm not saying no, but I just want a bit of time to consider what this might mean, OK?

Sure Mom. And thanks for not getting mad at me.

Jack? There is no reason for you to worry about me getting mad at you for your curiosity. A healthy curiosity is part of growing up. You just have to careful about where your curiosity might take you, to know what you could be getting into. OK, Jack?

OK, Mom.

*** –

I'm done my homework! Is there anything that I can do to help you in getting supper ready?

No, that's ok Jack, it's all under control.

I know Mom. You are great at doing it all, getting supper ready. But still, I would really like to get supper ready with you, if there is something that I can do. I want to stay in the kitchen and be in your company.

Well that's awfully nice of you Jack. In fact, yes there certainly are some things that you can do to help with getting supper together.

Before I start, would it be ok if I went and changed into the pretty bra that you got me for my birthday? I've only ever worn it in my bedroom and if you are ok with it, I would like to try having it on for supper time. Is that ok?

Well certainly it is Jack. I bought you your bra thinking that you would be wearing it freely at home any time that you might want to. I was wondering if you were ever going to spend time in it around me. I would love to see you wearing my gift.

*** –

Hi Mom.

Hi Jack. How was your time at Donna's today?

It was great. She and her Mom are really nice and I like getting my homework out of the way right after school with her. She is bright and is always great at working together to get it done in record speed. She picks things up pretty quickly, but I am able to help her understand things often enough too. We make a great team.

I am glad that you have found a way to keep your grades up in a way that is effective and sounds like fun too.

Yeah, it is that.

Mom?

Yes Jack?

I told Donna about my birthday present, you know, that bra that I asked you to buy for me.

Oh. And what did she think of that?

Well, after I described what the bra looked like, she went into her dresser and then gave me these.

Oh, my. They are pretty and look like a very good match to the bra. What are you going to do with them?

Well, if you are ok with it, I was thinking that I could wear them some of the times when I decide to wear my bra.

I wondered when you wanted to try wearing a bra if it would lead to wanting to try other girl's clothes too. That is why I had to think about it before saying yes to getting one for you. Yes Jack, if you want to wear pretty girl's panties when you wear your pretty girl's bra, I am fine with it. Just be careful not to draw attention to yourself that might get you hurt.

Thanks Mom. You're a great Mom.

You're a pretty great son yourself. And a very helpful one around the house at that, especially when you decide to wear your bra. Are you going to want a dress and a skirt and blouse too?

Really Mom? That would be pretty awesome. You would be ok with me dressing up sometimes in a girl's outfit?

If that is what you really want to do, I support you. I had a feeling that when I bought you the bra that you asked for, that it would not stop there, so sure. Would you like to go shopping on Saturday for an outfit or two?

That would be really cool! Er, Mom? Would it be ok if I asked Donna if she wanted to come along too?

Have the feeling that it may be a few years in the future that DONNA shall be picking out and evaluating ALL of Jacqueline's wardrobe as 'she' shall be Donna's sweetly submissive and feminine male girl wife!
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#12
(03-12-2018, 07:37 AM)sgbf Wrote: You're just in time for supper, Jack. How was your time after school at Donna's?

Hi Mom. It was fine. We finished our homework project and then played some video games.

That's nice dear. It is nice that you teamed up with her on your school project. She is one of the brightest students in your grade.

Yeah. I think I only beat her score on maybe two or three things the whole year. She always makes it fun to compete with her, teasing me when she does better, but always very supportive the times that I get a higher mark than her. I like her attitude.

Well she does seem like a very nice girl. Her mother is always cheerful, wherever I have seen her.

Donna was really excited today. Her mother took her out last weekend to shop for her first bras. I thought that most girls would be pretty private about the whole thing. But Donna is always so open about things. She was happy and thrilled and couldn't help but share her excitement with me.

Well it is a pretty special time for a girl, when she is ready to start wearing a bra for the first time. She is on the verge of being a grown woman. It is nice that she feels close to you and comfortable enough to show her excitement to you.

That's not the only thing she showed me. She took the two other bras out of her dresser to show them to me. She said that boys can sometimes be jerks, snapping girl's bra straps and teasing girls about their bras and she thinks it is simply because boys are curious about them and they never get the chance to really see what they are all about.

That's very forthcoming of her. Usually girls want to keep their underwear hidden from boys.

She did, Mom. I only saw the bras that she was not wearing.

Oh, I see. So then what did you think of them?

Well Donna showed me how it attaches in the back, and how the straps adjust and how the light padding in the front, even though it is pretty thin, can still make things smooth. Mom, I hope that you won't be mad, but I got swept along in all of Donna's excitement and when she wanted to show me how good the strap adjustments are to keep them from falling down and that this could only be demonstrated over a pair of real shoulders, well….

Well what dear?

Well, I hope that you won't be mad, but she helped me to put it on so she could show me how it all adjusts. I didn't have the bra on for very long, just so I could understand how it all worked. That way, she said, I would never have to act like a jerk, since I would already know all about how bras work.

That sounds quite logical. So do you now feel you are educated about girl's bras?

Well I certainly know more about them than I ever thought I would. I know what it feels like to wear one, even if it was only for a few minutes.

And how did it feel to you, Jack?

Well, it was weird having the band around my chest hugging me all the time regardless of any movement that I would make. And I could move my arms and shoulders up and down and the straps wouldn't budge holding the cups in place all the time. It was a strange feeling, but not uncomfortable.

Well Jack, bra straps are not uncomfortable when there is no weight to hold up. But if the straps are not wide enough, and the size of the breasts that they are holding up are heavy enough, then the pressure of the strap eating into your shoulders can be uncomfortable after wearing it for a whole day.

Yeah I suppose it could be.

Well that was very kind of Donna, to give you an education on girl's bras to keep you from acting like a jerk later on.

Yeah, well I'm just glad that I don't have to wear one all the time. 

*** –

Um, Mom?

Yes Jack, what is it?

You know that for my birthday I asked you for that video game and a new baseball mitt? 

I remember, dear.

Well I was wondering if I might be able to ask for one more thing.

What's that Jack?

I know this is going to sound strange, Mom. But I can't stop thinking about how Donna's bra felt when I tried it on. Do you think it would be ok for you to buy a bra for me, so I can wear it at home from time to time? I know boys don't need to wear bras, and shouldn't do that in public, or they would probably get beat up. It's just, I don't know, I'm still curious about how it might feel to wear it for a longer time. Is that too strange, Mom?

Well Jack, I don't know what to say. I never expected that my son would ask me for a birthday gift of a girl's bra. Do you want to become a girl? Do you like being a boy?

Mom! Of course I like being a boy and no I don't want to become a girl. I am happy being a boy. It's just. Well, I am curious about girls and girl's things. Girls are often nicer than boys, and well, they can look so pretty sometimes. They look and smell and feel nice, not like boys do. I just wonder what it would be like, having a bra hug me for a long time, and feel the straps over my shoulders too. You didn't get mad at me when I told you about the time I tried on Donna's bra, so I thought that it might be ok.

Hmmm, Jack. Let me think about it ok? I'm not saying no, but I just want a bit of time to consider what this might mean, OK?

Sure Mom. And thanks for not getting mad at me.

Jack? There is no reason for you to worry about me getting mad at you for your curiosity. A healthy curiosity is part of growing up. You just have to careful about where your curiosity might take you, to know what you could be getting into. OK, Jack?

OK, Mom.

*** –

I'm done my homework! Is there anything that I can do to help you in getting supper ready?

No, that's ok Jack, it's all under control.

I know Mom. You are great at doing it all, getting supper ready. But still, I would really like to get supper ready with you, if there is something that I can do. I want to stay in the kitchen and be in your company.

Well that's awfully nice of you Jack. In fact, yes there certainly are some things that you can do to help with getting supper together.

Before I start, would it be ok if I went and changed into the pretty bra that you got me for my birthday? I've only ever worn it in my bedroom and if you are ok with it, I would like to try having it on for supper time. Is that ok?

Well certainly it is Jack. I bought you your bra thinking that you would be wearing it freely at home any time that you might want to. I was wondering if you were ever going to spend time in it around me. I would love to see you wearing my gift.

*** –

Hi Mom.

Hi Jack. How was your time at Donna's today?

It was great. She and her Mom are really nice and I like getting my homework out of the way right after school with her. She is bright and is always great at working together to get it done in record speed. She picks things up pretty quickly, but I am able to help her understand things often enough too. We make a great team.

I am glad that you have found a way to keep your grades up in a way that is effective and sounds like fun too.

Yeah, it is that.

Mom?

Yes Jack?

I told Donna about my birthday present, you know, that bra that I asked you to buy for me.

Oh. And what did she think of that?

Well, after I described what the bra looked like, she went into her dresser and then gave me these.

Oh, my. They are pretty and look like a very good match to the bra. What are you going to do with them?

Well, if you are ok with it, I was thinking that I could wear them some of the times when I decide to wear my bra.

I wondered when you wanted to try wearing a bra if it would lead to wanting to try other girl's clothes too. That is why I had to think about it before saying yes to getting one for you. Yes Jack, if you want to wear pretty girl's panties when you wear your pretty girl's bra, I am fine with it. Just be careful not to draw attention to yourself that might get you hurt.

Thanks Mom. You're a great Mom.

You're a pretty great son yourself. And a very helpful one around the house at that, especially when you decide to wear your bra. Are you going to want a dress and a skirt and blouse too?

Really Mom? That would be pretty awesome. You would be ok with me dressing up sometimes in a girl's outfit?

If that is what you really want to do, I support you. I had a feeling that when I bought you the bra that you asked for, that it would not stop there, so sure. Would you like to go shopping on Saturday for an outfit or two?

That would be really cool! Er, Mom? Would it be ok if I asked Donna if she wanted to come along too?
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