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Thread: How has your dressing evolved since the first time you dressed?

  1. #26
    Platinum Member alwayshave's Avatar
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    I had a whole bunch of older sisters and a mother who kept her overflow in my room.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  2. #27
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    My introduction to wearing women's clothing was my mother's full slips. I loved the feel of the nylon. There was nothing sexual about wearing them which was only briefly whenI took them off the clothes drying washline. I also tried on her nylon nightgowns. As I got older I progressed to her bras, girdles, panties and hosiery. There was one sundress I could squeeze into. If I remember correctly trying on her clothes stopped when I outgrew her clothes.

    Several years later (5) when I was married I tried on one of my wife's nightgowns. That led to bedroom play as we purchased nighties and hosiery for me. After our first child was born my wife asked that I not wear the nighties in bed as our son's crib was at the foot of the bed....small one bedroom apartment. After we moved across country and finally bought a house I started to buy full slips and finally bras and panties. When my wife had a Sunday job for several hours I jumped at the "crumbs of time" as I called it. I got maybe three or four hours to dress every Sunday. About 1983 we finally had "The Talk."

    When my wife finally went back to work I would take off a "mental therapy" day from work and dress up. Ultimately I started buying dress and wigs and heels. It's been DADT. Over the years I have accumulated over 160 dresses and hundred of slips and panties..plenty of hosiery...and heels. As my wife has had several medical issues and surgeries my time to dress has been significantly reduced. No available time for full dressing so it is now wearing panties instead of my guy underwear and sleeping in a nightgown as we sleep apart due to medical/back issues.

  3. #28
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    Well I basically went from wearing my mothers clothes to buying and wearing my own clothes.

    As for styles and fashion, when I first started with my own clothes, I would wear and buy anything that fit. I never went out so it didn't matter if they went together or even looked good on me. I went through periods where I would obsess over a certain look or style secretary, hippy, ball gowns, elegant dresses, etc... Since I have come out as TG and actually spend time in public dressed, I try to only buy clothes that I will actually wear out in public. Jeans, shorts, cute tops, casual dresses and skirts in age and activity appropriate styles that I feel comfortable, feminine, and even sexy in when I am wearing them.

  4. #29
    Member Deedee_tv's Avatar
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    Like many here, I started with my Moms things until I was in my early teens and outgrew her. I’ve always had a job and money so once I graduated from college and moved to the big city, I started to explore. I kept it pretty low key for the 26 years I was married and raising children. I wore panties, women’s jeans and some shoes during those years. My ex was somewhat accepting. I dressed for several Halloween’s during that time, occasionally shaved my legs and began incorporating more female clothing into my daily wardrobe.

    Today I am divorced and do my own thing whenever I want. I am out to my kids and all of my best friends. If I’m not at work, I am wearing 100% women’s casual clothing in public. I have two walk in closets, one men’s and one women’s. I have at least 4 times more women’s clothes and shoes than men’s. I’m out to my hairdresser who colors, cuts, and styles my hair very feminine when I go to the shop wearing skinny jeans, cute tops and women’s shoes. I have embraced makeup and am getting much better. I’m often in full makeup and dresses at parties around my friends who are all comfortable with it and and know it is just my style. Yeah, I would say I have evolved a lot. ������

  5. #30
    Another fine dress AngelaYVR's Avatar
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    Since I first started fully dressing six years ago my style is finally able to reflect what I always envisioned: retro styles, quality fabrics, 50s aesthetic. It took some time and persistence to build up a good wardrobe. What I wore before was like experimentation and although it was ok and only slightly cringeworthy, I feel like my look has become more refined. I also don’t go out to the clubs anymore so I’ve given away all the mini skirts. Something that will never change, however, is the wearing of stockings under those outfits!

  6. #31
    Senior Member Asew's Avatar
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    As a teenager I would dress when I had the house to myself. It was always a small part of my life until I accepted it 20 months ago. Even since then it changes in terms of how often (more and more) and my preferences. And will continue to evolve

  7. #32
    Member Lucy23's Avatar
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    When I was a teenager, I would occasionaly dress in my mum's clothes, but stopped when they became small. Then it stopped for several years and resurfaced with my first girlfriend, then stopped again, and resurfaced in mid 20s to last until now. At first it was about skirts and tights, but has evolved to dressing as a woman from the neck down. I have found my style, and a nice wardrobe to accomodate what I need from dressing.

  8. #33
    Junior Member Robinadress's Avatar
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    In the beginning I borrowed clothes from my mother and my sister, and only when I was alone. As a child I would take a skirt out to the woods just to wear it outside. In my youth I started building up my own wardrobe. I started going more out, but everybody I read about was wearing wigs and makeup so I thought I also had to even though I only did it for the skirts and dresses. For the last ten years I have thrown away the wig and the makeup, and know I go out just wearing skirts, dresses and heels.

  9. #34
    Aspiring Shopaholic BTWimRobin's Avatar
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    For me it started as a young teen trying on mom's things snd experimenting with her makeup. Then suppressed it for a few years until my girlfriend at the time loved to dress me up. Suppressed it for some thirty years. A few months ago I finally, gave into my desire, came out to my accepting, supportive wife and now I am trying to get my look together. Still figuring it all out... and loving every minute of it.

  10. #35
    Miss Judy Judy-Somthing's Avatar
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    Wow it seems like most of us have similar stories!
    When I see my self I love it!
    "This is ME" I am not CRAZY, I'm just a GUY who likes dresses!
    Since allot of men dress up in woman's clothing that makes it a manly thing to do!
    Much more fun than fishing.
    I do construction like house building and I love CD-ing, what's the difference?

  11. #36
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    Hi Michelle , I have been in this program for over 72years now and
    I have a huge collection of clothes, shoes, lingerie, wigs & accessories,


    I would say that I have totally evolved into Crossdressing. >Orchid .oOOo.
    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 !! !!

  12. #37
    Member VS Fan's Avatar
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    Kindergarten: Halloween costume was The Hulk... which included green tights. I remember expressing my displeasure that they were girls’ tights but my mom convinced me that without them I wouldn’t be green. Memories are hazy but I believe I actually liked the way they felt.

    nothing for years and years...

    freshman in HS: at an all night gaming session at a friends house with a friend who had an older sister. During a break somehow I made it into her room and got a pair of panties out of her drawer. Kept those all summer wearing them off and on.

    Nothing for a few years

    senior in HS: discovered a pair of my moms nylons and tried them on... quickly put them back

    nothing for a few years

    sophomore or junior in college: my live in girlfriend moved out (break up) and she accidentally left behind a pair of VS second skin panties... wore them for a few days or a week before she eventually came and got all the other stuff she had forgotten and I threw those in the bag with everything else. (Still regret that! Lol)

    nothing for a few years

    Married after college and tried on one of my wife’s nighties when no one was home. Would buy nylons and wear them at night when traveling for work and throw them away before I got home.

    nothing for a few years

    married for about 5 years and I was transferred for a job - somehow ended up with a pair of wife’s panties (seriously was on accident) in my things... wore them constantly while I was in the new city before she moved up a few months later. Also discovered that I really enjoyed shaving my chest.

    nothing for a couple of years

    was on a business trip and stumbled into a Victoria’s Secret store in the local mall - bought a couple nighties and panties claiming they were for my wife. SA was beautiful and helpful. Wore them at night on that trip - I was now officially hooked. Collected a small stash of panties (10?) and kept them hidden in my home office.

    about a year later discovered a box of skirts and other things that were in the attic - started trying those on.

    moved again, and now I was working from home 100% of the time... got measured for some life insurance policy and when they measured me at 38” around the chest - I was like “oh....?” Found a bra of my wife’s from her pregnancy that was 38C... tried that on.... liked it. Jumped right into it and bought silicone breasts from fredericks of Hollywood...

    started buying my own clothes: skirts, tops, nylons etc....

    a couple years later later had a big bin full of stuff and finally realized that “uhhh I’m a crossdresser!!” Spent a lot of time browsing this site until I finally had the courage to tell my wife what was going on. Near disaster but we worked out the whole DADT thing.

    Went on like that for about 10 more years until various other things in our marriage caused me to move out and to another state for about 75% of the time... still married but who knows what will come. But I now sleep in what I want, wear what I want during the day (still working from home).... and while lonely I am at least content with this side of me.

    what a journey....
    Kelly a.k.a. VS Fan

  13. #38
    Senior Member JocelynJames's Avatar
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    Well , the first time I dressed it was hose, bra , dress and block heels , no makeup...and it was my mom’s. Now, it may be all those things, probably a bit more stylish, with makeup and a wig... and the clothes are all mine.
    If you only knew the power of the pink fog! ~Joss

  14. #39
    Aspiring Member Kaylin's Avatar
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    My dressing has also really evolved ALOT!

    Earlier this year when I came out to my wife that I was crossdressing. It freaked her out in a few different ways right away. Now she doesn't care and actually takes part. And loves her Kaylin time. As a kid, I started dressing when I was 12 years old. I seen my aunt wearing a fancy dress at a relative's wedding. A few weeks later I was at her house, and I put the same dress on with her panty hose and high heels and that's where it all started. She caught me dressing but she ended up being supportive of my Cding. I went off and on throughout the years dressing and doing/learning makeup. Ex girlfriends of mine used to find stockings and other things in my underwear drawers. But never had an issue with it. Other than steal my chick gear lol up until this year I really got serious with all of this. My wife actually is helping. She encouraged me to start shaving and all that. Now I have 2 full wardrobes. Its been an amazing experience. And still getting better. Now I'm actively in drag too. So I'm very thankful and grateful for all of this. And all of you wonderful ladies I've met on this forum with great advice too.
    Last edited by Kaylin; 08-08-2019 at 09:02 AM.

  15. #40
    Member Petra1's Avatar
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    My dressing started as a result of wanting to know what it was like to have breasts. At first, it was borrowing mom’s bra and stuffing with rolled towels. Gradually, step by step, moved up to full dressing in women’s clothes. Each step spurred on by my curiosity of “What would it be like if...” or “What would it be like to do _______ dressed or with breasts?” Now, Petra has her own closet full of clothes, shoes, wigs, breast forms, etc. I’m not a full-time dresser but more of a hobby dresser. Usually when I’m home alone though I have taken occasional drives in the middle of the day or to work when that involved leaving in the middle of the night.

  16. #41
    I like to be pretty Joanne Curl's Avatar
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    Like many, I started very young (around 8 or 9) wearing my mom’s clothes, pulling them out of the hamper. I graduated to using her makeup and teaching myself how to use it. I then started wearing her pretty dresses in the back of her closet. By 13 I was growing my hair long- it was in style then for boys. I started rolling a setting my hair after everyone went to bed and I’d sleep in curlers and setting solution. I’d wake up early and unroll my hair and I absolutely loved my curled blond full head of hair. I started buying my own ****ty clothes. Over the years as I aged I started buying appropriate clothes so I could go out and fit in. I’m still very much in the closet but when I do dress I try to dress age appropriate so I can blend in.

  17. #42
    Member Lux's Avatar
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    Similar story to others here. My earliest memories, I can remember trying on my mother’s pantyhose after being fascinated watching her put them on. I loved comic books and super heroes so around age 7-8, she let me wear tights, a danskin leotard and let me wear her boots so I could run around dressed up all day. That’s probably how this all started!

    I’ve always dressed head to toe but to answer the OP’s question, I’d say the the biggest evolution of my dressing is the regular use YouTube for make up techniques and the purchase of silicone hip pads and a breast plate I just started wearing. This gurl needed a little (ok, maybe a lot!) help with curves to hide the boy bod

  18. #43
    Junior Member StephanieIndy's Avatar
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    Like most my early experiences were with panties and tights, this expanded to wearing my sisters skirts and dresses.

    Now I have a full wardrobe and dress fem pretty much all day every day except for work where I wear a uniform, I am Trans but not out at work so still need to wear the male uniform

  19. #44
    Junior Member Jayne44C's Avatar
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    Started with Mother's clothes, shoes. It was a thrill, it was exciting. It's morphed over the decades. Now it's about looking as passable as possible but, I don't. It's about feeling comfortable with myself, not getting a thrill.

  20. #45
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    Started pretty tame but now I can underdress and feel confident. Wish I could pass as a woman

    [SIZE=1]- - - Updated - - -[/SIZE]

    [QUOTE=Kaylin;4384947]My dressing has also really evolved ALOT!

    Earlier this year when I came out to my wife that I was crossdressing. It freaked her out in a few different ways right away. Now she doesn't care and actually takes part. And loves her Kaylin time. As a kid, I started dressing when I was 12 years old. I seen my aunt wearing a fancy dress at a relative's wedding. A few weeks later I was at her house, and I put the same dress on with her panty hose and high heels and that's where it all started. She caught me dressing but she ended up being supportive of my Cding. I went off and on throughout the years dressing and doing/learning makeup. Ex girlfriends of mine used to find stockings and other things in my underwear drawers. But never had an issue with it. Other than steal my chick gear lol up until this year I really got serious with all of this. My wife actually is helping. She encouraged me to start shaving and all that. Now I have 2 full wardrobes. Its been an amazing experience. And still getting better. Now I'm actively in drag too. So I'm very thankful and grateful for all of this. And all of you wonderful ladies I've met on this forum with great advicei too.[/QU
    I too have seen some floral dresses that I got to later try on with pantie,hose,bra and girdle

    [SIZE=1]- - - Updated - - -[/SIZE]

    Love having breasts

    [SIZE=1]- - - Updated - - -[/SIZE]

    I also love perfume and full makeup. If I'm gonna be a woman I might aswell smell like on

    [SIZE=1]- - - Updated - - -[/SIZE]

    Kendra Sue is my ulter ego. I sometimes want to forget about life for a while

  21. #46
    Platinum Blonde member Ressie's Avatar
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    Even though my first CD experiences were ~60 years ago, I've improved during the last 10-20 years.

    Two things I haven't gotten into:
    1)false eyelashes. Can't get the hang of it and it's too frustrating to pursue.
    2)Hip/leg pads. When I look at a lovely GG in a nice dress I feel that padding can't quite get that look. I don't wanna try that hard to emulate a woman. But I love breast forms!
    "You're the only one to see the changes you take yourself through", Stevie Wonder

  22. #47
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    it started with going to my parents shower and seeing mom's pantyhose hanging to dry, probably age 10 or 12. Could help be feel them and try them on. I remember the first time, having no experience with pantyhose, I tried putting them on like a pair of pants, one leg at a time. What a mistake. Anyways, I figured it out and would put them one each time I took a shower.

    Then I found the pleasure of nudity and the crossdressing took a break through teen years, but in the mid 20's, it came back full force.

    On my days off, when the wife had to work, it was safe to dress and go out limitedly.

    Then kids came and the dressing was back on vacation.

    Now they are grown and i can dress again. The relationship has always been DADT, but she knows and thats what matters. No hiding or sneaking....

    Its as good as its going to get, but its enough for me.

  23. #48
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    When I was about 5 or so my mother put me in my sister's panties. I told my parents that I wanted to wear them all the time. They said no. I tried on my mothers clothes because I thought they were pretty. Like most of us I continued. When I went out on my own I began buying clothes and eventually going out dressed. I passed quite easily. I never wanted to be a girl, but enjoyed being accepted as one. As I got older I went through a lot of stages. People accepted me and I moved toward openly wearing women's clothes full time. As I've gotten old i don't try to look like a woman. I do wear casual women's clothes and underdress full time. Women give me a hug and feel my bra band. I haven't purchased male clothes in years. I do own a few dresses and have worn them around the house and to the neighbors. My neighbors have seen me wearing nightgowns and robes blowing in the wind to get the paper. Most all our friends are aware of my choice in clothes and I shop with my wife and several women who know. I don't wear forms, but women's clothes fit me better than men's.
    Last edited by lingerieLiz; 08-10-2019 at 10:56 PM.

  24. #49
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    I had a nice long paragraph typed and lost it somehow. So simply said, once my sister dressed me up totally in her school clothes, from panties, bra, girdle and nylons, slip, skirt and blouse, make-up and wig, I was so excited it stuck. She helped me to dress girly whenever I could. She used to take me to town en femme and look at clothes with her. It was fun to go in the ladies dressing room with her and try nice dresses and skirts on. It has been a great time dressing so ladylike and going out to ladies dress shops and getting help from many ladies to look real feminine.

  25. #50
    Member Cynthia_0101's Avatar
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    When I was younger I would dress and feel guilty after. I told my wife 5 months into dating and she saw me dressed once in 1998. Even though she knew and was accepting of it I was still not comfortabel with it so I would only dress while she was away or asleep. It was not until about 2013 that I was able to reconcile with myself that my dressing was not hurting me or anyone else and I should embrace it.

    Now I would spend lots of time dressed if I could find the extra time.

    Cynthia
    Be Yourself, And Be Fabulous While Doing it!

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