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Thread: How did you start dressing

  1. #26
    Member Jemima Stephens's Avatar
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    When I was 7 or 8 I went to childminders after school every day who had 2 daughters similar age to me. One day one of the girls spilt her drink all over me, so when my Mum came to pick me up I was in a pink T shirt, brown girl's trousers and pink knickers. I remember getting home and standing in front of the mirror not really understanding why it felt oddly nice.
    Needless to say the girls thought it hilarious so I got drinks spilt on me a few times after that!

  2. #27
    Aspiring Member Georgina's Avatar
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    It was over 60 years ago that my interest in female clothes began. I am not really sure how I started but, since I had no older sisters, it was my mother's clothes that attracted me. I remember beginning with slips and moving on to girdles and stockings. I was never interested in panties and, to this day, I still am not that involved. I wore only lingerie for a few years but eventually moved on to outer wear. Now at 68 years old I still wear a girdle, stockings and a slip with my dresses and skirts.

  3. #28
    Member Christina89's Avatar
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    I was about 12 or 13. I was watching a TV show called Totally Spies. I suddenly had an urge to go upstairs and try on some of my mother clothes. The first thing I tried on was one of her bikinis. I loved the feel of how it felt on my body. After a few minutes I took them off and went back to my normal routine for the night. The next day at school I couldn't get the thought out of my head. It was all I thought about. I couldn't get home fast enough to explore it further.

  4. #29
    Member Katherine L.'s Avatar
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    I got started when I was 11 or 12 and tried one of my mom’s bras I found in the clothes hamper. After that first time, I would regularly check the hamper to see if there were any bras I could wear. One time she caught me wearing one, but didn’t make a big deal of it. I was extremely embarrassed at the time, but not enough to ever stop.
    Last edited by Katherine L.; 08-09-2021 at 09:14 PM.

  5. #30
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    I had no older sisters or female cousins and no female playmates. As a little kid I did like the feel of my mother's nylon slips which I fondled and finally put one on. I loved the female of the material. Had no desire to be a girl. When puberty hit I found myself delving into my mother's lingerie drawer and wearing her girdles, bras, panties and slips. That lasted until I outgrew them.

  6. #31
    Gold Member Lana Mae's Avatar
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    At 4-6, a playmate flipped her dress over her head! That was neat! I wanted a dress! No, boys don't wear dresses!
    13 or so, mostly a sexual thing that lasted many years! It only involved panties! Once though, it was panties, bra, long leg panty girdle with stockings and a slip!
    Then married and wife didn't want another woman in the relationship! 34 years and 5 months later she passed away! During that time only panties 5 times and purged each time!
    Found this site and the rest is history!
    My little playmate that started it all was Lana!!!
    Hugs Lana Mae
    Life is worth living!
    "Foxy lady! You look so good!!" Jimi Hendrix

  7. #32
    New Member UsuallyRick's Avatar
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    As a youngster my parents friends were over with their daughters.. I was probably 8? We found my older sisters dress up clothes and got dressed up!! It felt great and I have since that day (or maybe longer ?) had a thing for stockings, dresses,panties etc .. liked the style and colors more than the drab Wranglers boys wear.. did I mention the girls and I got caught? Yup barely even a question and I admitted I liked it! Years later in high school I had some friends with hot sisters, I would steal their sexy panties and wear them,nearly got caught several times and accidentally left some in laundry, mom did my laundry and left them nicely folded on top of the pile.. I assumed she thought a girlfriend left them? Or not...?? I was that awkward size where boys pants were too short and men's were too big around so handmedown girls jeans became the norm.. then several years before my wife and I married we went to a Halloween party dressed as hookers.. now I can't get enough and have more skirts etc than guys stuff

  8. #33
    Aspiring Member jacques's Avatar
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    hello Kim,
    I started by wearing tights,
    luv J

  9. #34
    Senior Member BrendaPDX's Avatar
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    The moment when I knew I was hooked was when I bought a dress from the Salvation Army. It was a little on the modern side with beautiful colors and pattern, it fit perfectly, and when I looked into the mirror I knew I was hooked. I remember thinking a girl that pretty would probably never date me. LOL

  10. #35
    Aspiring Member LeannS's Avatar
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    It was 10 yrs ago I left a job and moved. It was a economical depressed area and I thought I had some pretty good job skills boy was I wrong. anyway moved in with a gal that would become my wife 3 yrs later. So I took on a role of a maid, chief bottle washer, cook and personal assistant. I thought hell if I am doing the part I might as well dress for it and so I did just so happens she was the same size as I am. The rest you might say is where I am at today Hair on, nails on and dressed to do the house cleaning leggings, knit dress and boots. Have a great day
    If you can't laugh and have fun you might as well go home.

  11. #36
    Silver Member CynthiaD's Avatar
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    I’ve told this story before, but ...
    When I was 3 I begged my mother to paint my nails with red nail polish, and she complied. I ran outside to show the other kids, but they all told me that only girls wear nail polish. I didn’t care. I loved the way they looked. And 69 years later, I still do.

  12. #37
    Member Dana3's Avatar
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    From as early as I can remember as a young boy, I've ALWAYS been strongly drawn towards girls ~ women and any all things related to.them and feminity.

    I never felt i.wss anything other than the person I was born. That is to say i wouldn't say I was nor suffered from gender dystopia.

    That was "part" of it ~ part of my internal make as an individual.

    I always preferred the company, companionship, being friends ~ playmates with girls ~ women.

    That to was part of of my internal makeup.

    I've always been somewhat envious ~ jealous of girls ~ women.

    When just entering adolescent ~ early on set of puberty i was drawn towards a need to experience and express feminity.

    First with my Sisters and Mothers lingerie, clothes and makeup, and later with that of girlfriends and later my first wife.

  13. #38
    Platinum Member alwayshave's Avatar
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    Started wearing my mother's and sister's clothes when I was 5ish years old.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  14. #39
    Senior Member mbmeen12's Avatar
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    I wish I had 5 bucks every time I'd see "THE" question lol. Ill bite, 12 yrs old apx give or take and wearing panty hose found in the laundry.
    Last edited by mbmeen12; 03-19-2021 at 12:16 AM. Reason: typo
    Escapism isn't necessarily bad, but is definitely unhealthy in the long term. While helpful in the short term, things will degrade over time. At some point, the escapee will have to face the issue. Things simply blowing over isn't really going to happen in many situations.

  15. #40
    Member HelpMe,Rhonda's Avatar
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    Another mission for when they invent the time machine, go back and tell young little me that someday people on computers will ask you multiple times about this scary thing you started doing so make sure you permanently remember the first time!

  16. #41
    ~ Bondage & Pantyhose ~ cosmolovesph's Avatar
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    I was probably around 7 years old and as a kid in the 70's into the 80's and the great time of Pantyhose everywhere (including mom wearing ) I was draw to the great tan nylon and once I got my hands on some (might have been laundry or discarded pairs dad used for gardening) I was in love. It evolved from there but mom was short (still is) and I had to get my own and that was probably in my later teens and just got more into women's clothing since. The first time I was able to wear some heels with pantyhose, I knew it was part of me and never looked back.
    ~~~~~~~~~~~~~~~~~~
    Crissandra
    ~AKA - Cosmo-Loves-PantyHose~
    Don't forget to compliment those wearing pantyhose, as to how nice their legs look!

  17. #42
    Life is more fun in heels Genifer Teal's Avatar
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    I had a really short teacher in 6th grade who wore really high heels to compensate. I was super curious how it was possible to walk in them. I mastered walking around the house in six inch heels in about a month. I quickly got bored. I wanted to go out and walk further in them. I couldn't do that without completing the look. That's how it grew.
    Last edited by Genifer Teal; 03-19-2021 at 08:41 PM.

  18. #43
    Senior Member Angela Marie's Avatar
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    I started by wearing my mothers tights (now called leggings) was I was about 10. Immediately hooked. At almost 67 they remain my favorite article of clothing.

  19. #44
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    My story is very similar to most. When 7 or 8 I started wearing my mother's slips. The feeling of silk against my skin was indescribable. It wasn't enough and I eventually began wearing my sister's panty hose, high heels, and dresses. The rest is history, as they say.
    "It is so easy to exist, instead of live. Unless you know there is a clock ticking."
    --Anna Quindlen, writer, journalist, columnist

  20. #45
    Miss Conception Karren H's Avatar
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    Quote Originally Posted by Katherine L. View Post
    I got started when was 11 or 12 and tried one of my mom’s bras that I found in the clothes hamper. After that first time, I would regularly check the hamper to see if there were any bras I could wear. One time she caught me wearing one, but didn’t make a big deal of it. I was extremely embarrassed at the time, but not enough to ever stop.
    My wife stopped putting her bras in the hamper because she thinks I would be in there trying them on... But I wouldn't... again... they are too big and she has really ugly bras... lol
    Current Obsession - Breasts and Lingerie!

    .......My Photos

  21. #46
    Aspiring Member Lacey New's Avatar
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    I think the seeds got planted in my early teenage years. Biology took over and I started to take an interest in the opposite gender. And back then girls wore short shirt to junior high school and it was not uncommon to se a glimpse of panties when one of the girls behind me sat down or got up from her school desk. I would imagine and wonder what was under those pretty panties. Well, I had a young mother and a sister who was only a year younger and we had a shared laundry hamper. And if I timed things right, I would usually have about a half an hour alone in the house after school. One day, I went to the bathroom and there was a pair of nylon briefs hanging out of the side of the hamper. So, out of curiosity, I put them on and the feeling was wonderful and exciting. Naturally, I took care of business. I felt guilty like I had done something completely forbidden and I said that I would never do it again. Well, that did not last long. Soon I was making sure I had that half hour alone as often as I could. Eventually, I got a little braver as well and figured out that if panties were exciting, then panties and a bra might be more exciting. It was. And eventually other lingerie as well. So, there was never any doubt that for me that dressing was a sexual fetish. The instant rush is gone, but it is still very sexual for me.

  22. #47
    Member Misty_cder's Avatar
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    When I was in my early teens, my mother would hang her aerobics tights and body suits in my bathroom to dry after washing them. Late a night, I would go in and enjoy the feeling of the fabrics on my skin as I put the garments on. My plunge into expanding my dressing started when I lived on my own after college. I would frequent adult stores to purchase lingerie and got dresses through catalogs. Thinking back on what I had, I would say my look was more on the trashy side. It wasn't until after I told my girlfriend (now wife) about my dressing did my outfits start to change and become more acceptable for my body type and, more appropriate, age. I would also say my dressing first started out as a sexual release for me. As I've gotten older, dressing has became more of a way to release the stresses of my career.

  23. #48
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    Hi Kim , Around age 4 I started playing with Mom's Stockings & Heels, >Orchid **OO**
    Having my ears triple pierced is AWESOME, ~~......

    I can explain it to you, But I can't comprehend it for you !

    If at first you don't succeed, Then Skydiving isn't for you.

    Be careful what you wish for, Once you ring a bell , you just can't Un-Ring it !! !!

  24. #49
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    I was started with my mothers clothing like thongs and bras.

  25. #50
    Oh to be an English Rose Jane G's Avatar
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    I have two sisters and five female cousins that I used to play dress up with. What chance did I have.

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