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I Remember My First Crossdressing Experience

Started Young

By: samctv10
Written on February 5th, 2012
By: samctv10
Age: 36-40 , Male
3,227 people have read this story

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47 responses
  • samctv10

    Sounds like you are a natural, so good for you

    Jan 11
    1 like
  • boyzwill8girlz

    Funny, since my sister's panties fit me till I was like 17, then switched to my mom's clothes, but I always wore a mix of both. Sister and her girlfriend dressed me up when I was nine....we played house. I was often the daughter, and loved it. Have loved dressing ever since!

    Jan 10
    2 likes
  • samctv10

    Ann, you do look so pretty, you should always be fem, and here's hoping your wife comes to see that

    Dec 23, 2012
    1 like
  • samctv10

    Hun, I neve have purged. I am me and this is how I need to dress. I enjoy feeling and being sensual

    Dec 21, 2012
    1 like
  • samctv10

    And you look great in your pantyhose, too, hun :)

    Dec 18, 2012
    1 like
  • sherrynpantyhose2k4

    I was hooked from the first time also. Started at age 6, now 54. Wonderful article, thank you for sharing.

    Dec 18, 2012
    1 like
  • samctv10

    I would love to hear, hun

    Dec 18, 2012
    1 like
  • Caleb22

    Sounds kind of like my story :)

    Dec 16, 2012
    1 like
  • samctv10

    Oh, you were really lucky, tghubby. Your mom was so good to you. Mine took a while to figure me out

    Oct 10, 2012
    2 likes
  • tghubby

    Ah yes, hooked ... I know what you mean. I was also about 7 when I tried on my first pair of panties, but they were given to me to wear by one of my two best friends, who happened to be girls. After that I asked my mom for panties and clothes like my friends and after a bit of conversation between us she started, buying me panties like my friends the next day. So I never tried on my mom's panties cause I had my own. Guress I missed something ...

    Oct 10, 2012
    1 like
  • samctv10

    you dirty boy, hehe

    Oct 10, 2012
    1 like
  • paige2000

    I luv dresssing in sexy lingerie as well,it feels so silly and sexy.just the thought of putting on something sexy makes me so hard

    Oct 10, 2012
    1 like
  • samctv10

    I think your wife might come around

    Aug 13, 2012
    1 like
  • 43454345an

    I remember trying on my mom's panties when I was about 6, got very excited, loved the silky smooth material against my skin. Dreamed about being a girl for quite a few years. Then at about 10, I dressed as a girl for Halloween, skirt, blouse, stockings, and wig with some makeup, mom dressed me, the neighbors could not guess who I was, and this thrilled me, they thought I was a girl from another block. Now after 40 years I am still dressing with help from my wife. I still get excited, wear panties and nighties always, and love to spend the day around the house with just us girls.

    Aug 12, 2012
    2 likes
  • tam19

    Like you, there was something very special about my mother's panties when I put them on. I don't know weather I related them to panties that a grown-up wears, or just what made them special. I do know that she wore only Vanity Fair nylon briefs, and to this day they are my favorites too. I like the feeling of tight leg eleastics, and being covered completely. I could never enjoy thongs, how can they be called panties? Today I love to dress as a professional women..having conservative lingerie, white nylon brief panties, a bra with a little feminine touch, garter belt, half slip, and stockings, a two piece tailored women's suit, with a white or pastel nylon blouse underneath..and of course heels. I don't know why, but when I;m dressed, I feel a sense of female power. Hard to explain, I know.



    Tam19

    Aug 7, 2012
    1 like
  • samctv10

    Oh, I know, as opposed to rough men's underwear

    Aug 4, 2012
    1 like
  • tam19

    There is something about wearing panties, weather under male attire, or under a skirt or jeans. I know when I wear panties, my whole mental and physical feelings change. I am more at peace with myself. I find that I don't care if I am doing something that others would call me a sissy for doing. I am at peace with myself. I know that I am not interested in becoming a female, although when I am wearing female clothing, as I said, something changes within me. I like the change, I like myself more, if that makes sense.

    Jul 29, 2012
    3 likes
  • Inkspell

    I started to 'borrow' my mom's stockings and garter-belt when I was 12. I'm 56 now. I'd put on a bathrobe, hike it up to mini-length, and look at my legs in mirror. It was like -- wow! I'd spend hours ************ while looking at myself.

    Jul 27, 2012
    1 like
  • spaz1177

    it is great to have sisters you can borrow from

    May 12, 2012
    1 like
  • rockynook

    My sister started dressing me at about age age 7 or 8. This continued until I was 15.

    I dressed on and of from 16 until 10 years ago.

    My wife and I are in a FLR, and remain dressed for her pleasure.

    Feb 25, 2012
    2 likes
    • PJJA1000

      What does FLR stand for?

      Jan 12
      1 like
  • jamiesissycd

    I have the same feelings sweetie. I started young, around 8. My Mom dressed me completly like a girl for a school Halloween party. I didn't understand the erotic sensations and feelings, but I too knew I liked and enjoyed it.

    Feb 21, 2012
    2 likes
    • samctv10

      I just dressed myself and am not sure why

      Feb 22, 2012
      1 like
    • tam19

      Jamie, my mother dressed me one Halloween. This was during the time that I as experimenting with wearing her panties, around eight or nine years of age. She bought me a proper skirt and blouse, ones that would fit me..but I remember how disapointed I was when I found out I was not going to be wearing panties. My mother just kept my boys undies on me. How much i want to feel the panties on underneath my outfit...

      Tam19

      Aug 7, 2012
      1 like
    • jamiesissycd

      My Mother dressed me completly as a girl, stockings, garterbelt, panties, bra, slip, low heels,wig, and full make up. After the party I didn't want to take the clothes off. The feelings and the sensations I was getting was so wonderfull. It was the first erection I think I ever had. She did make me take everything off. But I always sneaked away and put on panties and a bra with a slip. Stopped when I went into the Army, then started back after I got out. I still love and enjoying wearing womens lingerie today at age 62. And do every day.

      Aug 7, 2012
      1 like
    • tam19

      Jamie, you were really lucky to have such an understanding mother. Perhaps she knew what it would mean to you, to be able to experience the entire feminine dressing up. For me, now if I'm not properly dressed, panties, bra, etc..I can sense it immediately. Do you or anyone, think when you began to dress, began to feel those special feelings and thoughts..it was more exciting then, then it is now, when we are older. I know myself, I often look back and think of the times I dressed when I was very young, and also as a teenager.

      Tam19

      Aug 8, 2012
      1 like
    1 More Reply
  • samctv10

    Thanks

    Feb 15, 2012
    1 like
  • samctv10

    And then you were a transvestite for life, right?

    Feb 14, 2012
    1 like
  • samctv10

    You should do it. I bet you both love it

    Feb 13, 2012
    1 like
  • samctv10

    Thank you, both, for your comments and comliments. It is so sensual, isn't it?

    Feb 11, 2012
    1 like
  • silkgirl8

    A wonderful feeling of softness next to the skin, I wear silk french knickers every day.

    Feb 11, 2012
    1 like
  • samctv10

    Thank you for your comment, nicely written as well. But now you are back crossdressing, so good for you. I bet you were sorry when your sister left, taking your wardrobe with her.

    Feb 8, 2012
    1 like
  • KarenStm

    Nicely written sam describing you first crossdressing experience and your thoughts about it. I started about 10 with my sisters clothes she was about 6 years older than me and had some pretty girlie sunsuits I loved to put on, I also loved wearing her babydoll nities, When I was about 15 she got married and moved out taking her pretty girlie clothes with her so I stopped crossdressing for about 15 years.

    Feb 8, 2012
    2 likes
  • LapiudolceTS

    Live and love as you are, not as others percieve you to be. It is our choice. I am happy for you to be yourself, by your own definitions.

    Feb 8, 2012
    1 like
  • samctv10

    Wow, you really went all in the first time. Good for you!

    Feb 7, 2012
    1 like

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