I Remember My First Crossdressing Experience

I Told My Mom

By: XDressingIsGreat

Written on November 3rd, 2012

So I finally talked to my mom about crossdressing.I was sitting in my room and I really wanted to put on some of her clothes sooo bad. So I sent her a text asking "Can I put on some if your clothes? Im still crossdressing the only reason I lied to you before is because I didnt know what your reaction you would of had. This also took alot to send this to you." I was so happy when I sent that text a few minutes later I got a rext from her saying "I still dont know how I feel about it and I bet it did." and I was somewhat sad but I replyed "I understand and it did." she never replyed back nor answered my question so I sent her a text asking "So can I?" and she said "Uh no for now." I was sad when she said no although I was happy when she said "for now." But when I can I cant wait to put on a womens suit, panty hoes and some heels<3 So thats another story so I guess come back for more.

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By: XDressingIsGreat

Age: 13-15 , Male

1,734 people have read this story

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36 responses

silkennylonsecrets

Wow, at least she isn't freaking out about it. My Mom would have freaked and probably sent me to a shrink if she knew. But my dressing was more about sexuality than comfort, and I am not gay, submissive or sissy like either. Its more like a lingerie fetish myself.

Nov 5, 2012
2 likes
- XDressingIsGreat
  Well actually I told her awhile ago more like 3 mabey 4 months ago and she wanted me to talk to someone. And she said not a shrink. And I knew exactly that she ment a shrink. I told her I would talk to someone but my dad cant know and she said well dad would have to know so then we just dropped it. Until a few days ago.
  
  Nov 5, 2012
  1 like
Stormofarrows

i wish i could just ask that to my mom but im still in th closet. add me if u want to talk

Nov 4, 2012
2 likes
- XDressingIsGreat
  Im sorry, I never notice your comment. I know and so sould many other XDressers that its pretty hard to tell your mom. It took me awhile to tell her and alot of thought of how she would react.
  
  Nov 5, 2012
  1 like
SilkandLace

why don't you get your own things, if I may ask?

Nov 3, 2012
1 like
- XDressingIsGreat
  I dont really know how to ask. I know shes going shopping soon at the mall and in not going but I really hope that she may get me some of my own things.
  
  Nov 3, 2012
  1 like
- SilkandLace
  no, I mean YOU go get what you like?
  
  Nov 3, 2012
  1 like
- XDressingIsGreat
  Well im gonna ask in a few months after I know if she is fine with it. But I love wearing her suits, panty hoes, abd her heels.
  
  Nov 3, 2012
  1 like
- SilkandLace
  no, I mean go and buy what you like!
  
  Nov 3, 2012
  1 like
- XDressingIsGreat
  Well im 15 and it would be weird buying panties and bras. Not what a normal 15 year old boy does.
  
  Nov 3, 2012
  1 like
- SilkandLace
  I did, panties, buy what you like with your money!
  
  Nov 3, 2012
  1 like
- XDressingIsGreat
  Yea, but I havnt been working cause I have school now.
  
  Nov 3, 2012
  1 like
- SilkandLace
  ok, I understand, I bought a pair of satin panties when I was 11, yes probably weird, but I got them and left the store to enjoy!
  
  Nov 3, 2012
  1 like
- XDressingIsGreat
  Well thanks for you advice.
  
  Nov 3, 2012
  1 like
- SilkandLace
  I hope you succeed and enjoy like I did, a big step, but I used to steal panties and lingerie and almost got caught, much more wonderful when I bought it and it was all mine!
  
  Nov 3, 2012
  1 like
- XDressingIsGreat
  Well I have another story about steeling lingerie if you would like to read that.
  
  Nov 3, 2012
  1 like
- SilkandLace
  I would, but I can't add you
  
  Nov 3, 2012
  1 like
- XDressingIsGreat
  Its in this catagory the title of it is called "Can I do it?"
  
  Nov 3, 2012
  1 like
- SilkandLace
  theres alot there, its ok, I just basked in buying my own lingerie, so much fun!
  
  Nov 3, 2012
  1 like
- XDressingIsGreat
  Well to basically sum it up can I steel a thong that is just siting on the floor and brad that are always in the bathroom, i know its illigal tho. (just 1 mabey 2 bras and a pair of panties or a thong.)
  
  Nov 3, 2012
  1 like
- SilkandLace
  not sure what you mean, but enjoy what you can, crossdressing is wonderful, get yourself some lovely dainties...
  
  Nov 3, 2012
  1 like
- XDressingIsGreat
  Can I steel it? I know it illigal though...
  
  Nov 3, 2012
  1 like
- SilkandLace
  nooooo! I'm saying don't steal, buy you lovelies!
  
  Nov 3, 2012
  1 like
- XDressingIsGreat
  Okay. Thanks for your advice. Later.
  
  Nov 3, 2012
  1 like
- SilkandLace
  see ya
  
  Nov 3, 2012
  1 like
- andreaneejustinfield
  Listen to SilkandLace and I, you really should go to a store and buy your own lingerie. You want silky lingerie and there is nothing wrong with you having it. There is so much choice to them. Add me and I can help you with that. Your sweet and I would like to help you be happy.
  
  Nov 5, 2012
  1 like
18 More Replies
CDralph2010

Until she's willing to let you, try to avoid taking her things without her permission. That will TOTALLY destroy the trust between you, and she's likely never to accept or understand you after that. No matter how careful you think you are, she WILL notice. Don't destroy your relationship with the one person you were able to trust with your secret.
It may mean doing without for weeks, months, or even years. I know; I've been there. I had to wait until I was an adult living on my own before I could start dressing again... but you know what? I survived.
Hopefully once she's had time to think about it she'll be more open to it. You also need to think about what it means to you. She may be worried that you are gay, or that you are using her clothes for sexual relief, or that you want surgery to become a woman. You should be prepared to tell her the answers to those, which means you have to know the answers yourself.
I really caution against relying on clothes for sexual satisfaction. What that does it create a link in your mind between the clothes and the pleasure. Repeat that enough, and it becomes reinforced to the point that a healthy physical relationship with another person is impossible. Instead do your regular day-to-day activities while dressed: Do your schoolwork, watch TV, text your friends (haha, if they only knew what you're wearing!), etc. That way you associate the dressing with tranquility and stability in your life. Much healthier in the long term, IMO.

Nov 3, 2012
2 likes
- XDressingIsGreat
  She has already asked me if im gay I said no cause im not and iv never used it as sexual satisfaction because iv never felt the need to. The only reason I Xdress is because to me womens clothes ate cunfy, and fun to me to wear around the house.
  
  Nov 3, 2012
  1 like
- CDralph2010
  Ah, looks like you've already thought it through. Well done! I do hope the two of you can work it out together, then.
  
  Nov 4, 2012
  1 like
- XDressingIsGreat
  Yes. Yes I did.
  
  Nov 4, 2012
  1 like
Melodie13

She didn't say no which is good. Now you need to dress and present yourself to her in person.
Put on a dress or a skirt, whichever you feel most comfortable in. Make sure you have proper undies on too. Tell your mom this is what you want when you present yourself. You won't go out without permission so she hadn't worry about being embarrassed. Promise to do it also when you want to dress.

Nov 3, 2012
3 likes
- XDressingIsGreat
  I can only wear her clothes because I dont have my own and her skirt dosnt fit me. I like to wear her gray womens suit pants, a black cowl neck sweater with a gray coat over it, black high heels and the underwear that I wear of hers is a black bra and a pair of her black panties also a pair of panty hoes...Would that be presentable?
  
  Nov 3, 2012
  1 like
- Melodie13
  yes, but you could pin the skirt at the waist so it fits you a bit better. Then turn the pinned portion to your left side or around to your back. Even if the skirt is a little long it will be okay.
  
  Nov 3, 2012
  1 like
- XDressingIsGreat
  I guess ill just wear what I had mentioned. It would just be easier on me.
  
  Nov 3, 2012
  1 like
- Melodie13
  ok, maybe after you could convince your mom to take you shopping for a couple of skirts. You could tell her she could get them cheaper at a thrift store since they are for home use only. Most are practically new as well, plus it could save her money over what the regular stores charge.
  
  Nov 3, 2012
  1 like
- andreaneejustinfield
  Please friend me and look at my many albums with boys in dresses, skirts, panties, and tights. They will help you with ideas about what you would like to present yourself to your mom. Like Melodie13 said, there are so many options to what you would like to dress in.
  
  Nov 3, 2012
  1 like
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I Remember My First Crossdressing Experience

I Told My Mom

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