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Thread: When did you first crossdress?

  1. #501
    Member LenGray's Avatar
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    Can't remember exactly when, but I know that when I was little I was in LOVE with my brother's cargo pants and band shirts. My mom was always trying to get me to wear cute dresses and skirts but I was constantly going into my brothers closet and getting his clothes instead lol I didn't realize that was cross dressing back then though, I just knew that I was so much more comfortable in them This continued pretty much until he moved out to live with his girlfriend.

    I was about 15-16 when I dressed with the intention of being perceived as a boy. I hated my sex a lot back then and I'd just moved to a new town so I figured, why not? I liked the feeling that I got from it I felt very sure of myself, much more so than when I dressed as a girl. Since then, I've kind of been waffling between the two lol

  2. #502
    New Member Laura's Avatar
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    Well for me it started when I was about 11.

    My friend told me that he used to put on his mums shoes and dance to Human League records. I tried that with my sisters shoes, loved it, and decided to take it one step further. She had a beautiful powder blue bra with matching knickers and suspender belt. How could I resist? And when I saw that she had white stockings in her drawer too, well that was enough for me. Although she didn't have a name at that stage, Laura was born.

    She has been a secret ever since but I'm hoping to get some tips and advice from the girls here and see if I feel like.........................who knows what!

    Time will tell.
    Laura

    Probably the most gorgeous truck driver you'll ever meet!

    Love the shoes!

  3. #503
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    I must have been around 6 or 7 when I started having a strange interest in wearing tights. It took off after that before I started dressing seriously when I was 14

  4. #504
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    One of my earliest memories, not just in crossdressing but really in life, was being in pre-kindergarten and putting on this ballerina tutu I found in the toy box. Who would've thought that little, innocent action would have led to all of this.

  5. #505
    Discovering the Gurl Xandra's Avatar
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    Minj skirts from cut-off jeans. Love it.
    Quote Originally Posted by Kate Haylette View Post
    Hmmm, not sure if mine counts....but my mom was the
    oldest of 4 sisters. One was still pretty young. They
    weren't a well-off family, so when i was brand new, for
    my first few years, my clothes were hand-me-downs
    from the sisters.



    My mom told me that years later. I do vaguely recall
    sitting under the ironing board in the half-assed shack
    we lived in and one of the sisters teasing me about the
    little dress i was wearing. Playfully, of course.

    On my own was about 8. I didn't know or care about
    anything to do with sex....i just liked the clothes.

    I made several mini-skirts from just cut-off jeans for
    years after. I could make them whenever i wanted
    a new one.

    ~♥~
    Last edited by Katey888; 02-20-2014 at 08:09 AM. Reason: Corrected Quote box

  6. #506
    Member Aeslyn's Avatar
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    Was thinking about this topic just recently trying to remember. Unfortunately I don't. But I do remember that is was such a secret part of my life, my secret pleasure, by the time I was 8. Somewhere around that age there was this one day my cousin who was my age suggested we steal some panties from a clothes line and wear them all day everywhere we went (it was a small town and kids of that age had a lot of freedom). This is the first specific memory of wear anything girly. How I know I was already into wearing that stuff though is that I distinctly remember how excited I was by his idea and how much I felt that I had to hide my excitement lest he learn my dirty little secret.

  7. #507
    New Member dressyjessy's Avatar
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    I started much later. It wasnt untill i was 21 when my girlfriend would leave some cloths at my house, well my parents house. I started wearing her panties. Not too much later i bought my first pair of heels from Payless. Oh, ill never forget how it felt the first time i put them on.

  8. #508
    Discovering the Gurl Xandra's Avatar
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    Aeslyn: I love your story.
    Last edited by Xandra; 02-19-2014 at 01:29 AM.

  9. #509
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    I think I was 8 or 9. My mother had left some of her clothes lying around and had gone to work. I was home with my sisters, and went into the bathroom and tried on a blouse (nylon or silk) but very smooth and sensuous. I loved how it felt and looked! Then my little sister burst into the bathroom. Some fast talking satisfied her curiosity, and I was glad because I knew even then I needed to keep it secret. But i was hooked, and have been dressing ever since. In secret for many years, but came out to my wife about a year ago...

  10. #510
    Member Aeslyn's Avatar
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    Quote Originally Posted by Alexandra Santora View Post
    Aeslyn: I love your story.
    Thankies

  11. #511
    New Member Nadina's Avatar
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    Panty hose age 11? 12? then panties and a skirt that was my aunts around the same time, There is something about wearing panties and a wispy skirt for me, the way the air feels around my legs when the skirt moves around brushing against me, I feel like a different person with a skirt on.

  12. #512
    Junior Member longirl's Avatar
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    I was 5 and my Cousins were living at our house and i have a cousin that is a few weeks younger then me and i took all of her panties, that is also the first time i got caught because she had no panties and they found me wearing them.

  13. #513
    Junior Member kiwidownunder's Avatar
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    Around 6 years old ,at a friends party his sister was a lot older and got us to dress in her old cloths
    Felt wonderful!


    kiwi

  14. #514
    Pretty in Pink Barbie Anne's Avatar
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    Quote Originally Posted by longirl View Post
    I was 5 and my Cousins were living at our house and i have a cousin that is a few weeks younger then me and i took all of her panties, that is also the first time i got caught because she had no panties and they found me wearing them.
    I already posted the story in this thread but the short version is DITTO lol. Glad I wasn't the only one
    Barbie

  15. #515
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    Probably around 12-13 years old, still to this day always been just me...long time closet cd.

  16. #516
    Part time CD girl Lexi Moralas's Avatar
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    I was 11

  17. #517
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    Way back December 2007, I posted this on the board. Seems that it fits in here. My mother has since passed away.


    I posted this before, but it seems appropriate for this thread.

    My mother is now 79 years old and lives in a house my wife and I bought for her that is two doors down from us.

    She is still a wonderful lady, getting older and just got her 25 year pin from AA. When I was growing up, I never knew she drank, just thought that everyone occasionally found their mother passed out at the kitchen table with a half empty bottle of scotch. I'm much better now, thank you.

    I was around 9 years old.

    My 15 year old cousin had moved in with us. It was a sad story, her mother had died, her father remarried, the typical wicked step mother, car wreck, her father died and the step mother went into a nursing home.

    Somehow in my 9 year old mind, I thought she (the cousin) was getting favorable treatment from my parents. I wanted to get the same kind of treatment.

    For some reason I thought if I wore her clothes, my parents and grandparents would shower me with affection also.

    I put on a pair of her yellow big panties (this was about 1958) and a pair of her side zip jeans. Nobody even noticed. (In retrospect I don't see how they could not have known, but they didn't say anything to me at the time.)

    One time when my parents went on a trip and the cousin was in charge of us. She was downstairs reading a book. I got on a pair of her panties and crawled into her bed. (In our house it was scandalous to sleep in anything but pajamas or a nightgown.)

    The cousin came upstairs and turned on the light in her bedroom and saw me in her bed. I feigned being asleep. She came over and ever so gently lifted up the covers and saw me in her panties. The covers came back down, she turned out the light and went and got into my bed.

    After a while, I went into my bedroom in just her panties. She was in my bed reading a book. I told her I was scared and wanted someone to hold me. She looked at me and told me to go back to bed and hold myself.

    The episode was never mentioned again.

    She eventually went away to college.

    Fast forward about 5 or 6 years. I had developed a bedwetting problem. Wet beds and wet sheets were a real bummer.

    My father insisted I was just to d*** lazy to get out of the bed to go to the bathroom. Lots of tears, spankings and wet pajamas. My mother eventually bought me several pairs of 'stay dry' incontinent pants that I was to wear under my pajamas. I was both embarassed and excited about them at the same time.

    My father had remodeled our basement and turned it into a bedroom. I was down there by myself, had a tv and radio and my school desk where I did my homework.

    I had progressed to buying my own panties by this time.---this was before walmart and kmart. Went to Kresgee's or Woolworths to get them.

    One night I was in bed in a just a pair of panties.

    My mother came downstairs to kiss me goodnight. My pajamas were lying on my desk, along with some laundry she had told me to put away earlier in the day.

    She told me to get out of bed and put away the laundry like she had told me to do. I told her no, could I do it in the morning, I was tired.

    Mother insisted I do as she told me to do. Then she saw my pajamas and wanted to know why I didn't have them on and did I have on my 'protection' (That was our code word for the incontinent pants and diapers I wore to bed....we would NEVER call them by their real names, only by protection.)

    Mother than told me to get out of bed right now. I refused. She reached down to pull my covers off of me and I blurted out, "Mom, I'm naked!"

    She went over to my desk and picked up my pajama bottoms, gave them to me and told me put them on and put away the laundry.

    I put the bottoms on over my panties while still under the covers and got out of bed and started to put away my laundry. She then insisted I wear protection to bed and I was always to wear protection and pajamas to bed. Nice people didn't sleep without pajamas.

    She then swatted my butt. She must have been able to tell I had something on under my pajamas because she pulled out the waistband and asked me what I was wearing.

    I started crying. I told her it wasn't fair, I hated wearing protection, I hated having to wear big white briefs (JC Penny double seats--wish I had some now..she bought them for me) that looked like diapers, I hated wearing diapers to bed and I liked how these underpants felt. I told her I had bought them thinking they were boy's bikini underpants.

    She hugged me and said she understood how I felt. But until I outgrew the bedwetting it was so much easier on her to have me wear protection. It was too much trouble to have to laundry everyday--we didn't have a dryer- and to wipe my face and put on my protection and go to bed.

    And she stood there. I didn't know what I was supposed to do. I was too embarassed to pull of my pajama pants and have my mother see me in panties. I had only occasionally put on my protection in front of her, never in front of my father.

    Finally I said the heck with it, sat on the bed and took of my pajama bottoms. I then walked over to my desk in my panties and turned my back, took off the panties and pulled on my protection.

    This was very exciting to me and I didn't know why.

    I started to get back into bed and my mother asked if I was forgetting something. I started to put on the pajama bottoms. No, my mother said, finish putting away the laundry.

    I put away the laundry in my chest of drawers just wearing my protection. I was so embarassed and excited at the same time and didn't know why.

    When I was done, my mother came over and kissed me and said, 'don't forget your pajamas." and went out the door and turned out the light.

    Oh man, I knew I was in trouble. Not only was I a bedwetter, but my Mom had found out I wear panties. And she was probably going to tell my dad. I worried about that until I fell asleep. I think I cried myself to sleep that night. I wished I had on panties instead of protection.

    The next day when I got home from school, I was in my basement room lying on my bed watching TV. My mom came downstairs with a bag from Sears.

    She sat on my bed and said she loved me and was so proud of me for being a nice young man. She told me she was sorry that I struggled so much. She knew I was a good kid. Things will get better she said. Then, as she leaned over and hugged me, she said, "I understand boys need their privacy," and handed me the bag. "These are for you", she said.

    Somehow I knew I had the upper hand. I just laid there and didn't return her hug or take the bag. She got up, left the bag on my bed, said supper will be ready when your father gets home and went upstairs. At the top of the stairs, she turned and said to me, "I am not going to mention this to your father."

  18. #518
    All girl, all the time! ❤ Felicia Dee's Avatar
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    Hi Alexandra! Thanks! Now if I could just find some local grrls to hang out with...

  19. #519
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    Around 13 I had one afternoon by myself every week and my mom used to store her used pantyhose in a plastic bag. I started wearing wool tights I used to wear during ski trips, and then the pantyhose in the bag and became hooked to pantyhose. I bought my first pair 10 years later.

    It took 20 more years after the first episodes for me to turn to other aspects of crossdressing, involving stockings and garter belts, skirts and dresses, knickers and bras, and now ballet flats and heels.

  20. #520
    Junior Member FemPossible's Avatar
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    I remember I was like 10 or 11 and my sisters dressed me up as a girl. It wasn't very detailed (like panties or bras), just a wig, a little makeup, tight sweatpants and a blouse. While it may have just been a bunch of goofing around, I felt really comfortable in those clothes.

  21. #521
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    I'm hoping to start in the next week or so. Finally worked up the courage to buy clothes.

  22. #522
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    My grandmothers pantyhose and my moms heels. I still look for that wonderful round toe looking pumps. But I feel so ashamed when I go to a store thats crowded and look around at the heels. Anyone else feel that way??

  23. #523
    Aspiring Member GenieGirl's Avatar
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    When I was around 5. I first got caught when I was about 9 by my mom. She didn't like it. Afterwards years of off and on cding trying to repress it from then on up until about 3 years ago when oi said to heck with it!

  24. #524
    Aspiring Member Jenny Elwood's Avatar
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    I was between 4 and 5 y.o. My brother and I wanted to dress up in my parents clothes. We "fought" about who would get to wear my fathers clothes. He is older than me so he reckoned he should have first choice. I "reluctantly" relented. I never let on that I was glad to be the younger.

    I think my mom still has this out of focus picture of two little scarecrows out on the lawn, one is wearing a slip.

  25. #525
    New Member Truth's Avatar
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    First time I CD was when I was about 13 or 14, whilst my step mum was out!

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