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Thread: Can you remember the first time you put on a dress ? What it looked like, whose dress

  1. #26
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    For me, there is something about being zipped in, that is appealing.

    I bought a short black bodycon skirt (not knowing what bodycon was) but was disappointed with no zip, so binned it and bought another short black skirt and made sure it had a zip.

  2. #27
    Banned Read only Cass42's Avatar
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    Age 7,was a dark navy sleeveless dress.Mom and I were at an aunt's house visiting and I discovered it on the floor deciding to try it on

  3. #28
    Claire M Claire M's Avatar
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    I don't remember my 1st dress but I remember every detail of the first time I fully dressed. I was 13 and had tried on my sisters panties a bras a couple time before. One day I was home alone so I tried on one of her favorite outfits, a green wool skirt with a white sweater top. I added some panty hose and a pair of heels. I remember looking in the mirror and my emotions going everywhere .. I felt really good wearing them, I definitely didn't want to take them off ... ever ... but I also didn't want anyone to ever find out I had done it. (a cycle I seem to repeat even to this day sadly)

  4. #29
    Lacy Lacyfem's Avatar
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    I definitely remember the first time I put on a pantie and bra as I was 10, so I'm guessing the dress came in my teens as my start was more into the lingerie.
    Lacyfem

  5. #30
    Platinum Member Beverley Sims's Avatar
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    Ilooked like a boy in a dress, I was five.
    Work on your elegance,
    and beauty will follow.

  6. #31
    Member Deborah G's Avatar
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    I'm sure it was one of my sister's wool skirts, along with a fuzzy, cropped sweater top. I tried it on after putting on her panties and bra, and It fit me perfectly. But, I of course needed to stuff the bra a bit to get the right look! I was 14 or 15 at the time.

  7. #32
    Member Christina89's Avatar
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    I was about 18 or 19. I was staying at my dad's for the summer. At my dad's my aunt also lived there too to help take care of my grandparents that lived there. Well I had the basement to myself and my aunt left some of her clothes that wouldn't fit in her closet down in the basement. I went thru them one night and found her old wedding dress. Her and I were about the same size so I figured why not. I tried it on and it felt amazing. Sadly I didn't get any pictures of it at the time. But I have the memories.

  8. #33
    Aspiring Member Robbiegirl's Avatar
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    Lots of Great answers ! Thanks ! I am a bit surprised no one mentioned ever trying on Tennis Dresses ! As got older my sisters had some very cute, white short tennis dresses that came with bikini panties with a few rows of ruffles ! So fun to put on and pretend to play tennis in. Did anyone else ever try one on ?

  9. #34
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    Robbiegirl
    There is a line......
    And you have crossed it 😮

    Only kidding😂
    No but I did used to fancy Chris Evert and Jennifer Capriari

  10. #35
    Silver Member Pumped's Avatar
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    I don't remember trying on a dress until about 8 years ago. I bought a scuba fabric, with blue and white strips, flared skirt, sleeveless tank style. I love the feeling of tight clothes and this one fit snug.

    What did I look like? Like an old guy in a dress with fake boobs! It was a bit disheartening!

  11. #36
    Silver Member CynthiaD's Avatar
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    I was in 7th grade when I dressed fully for the first time, dress, bra stuffed with socks, full slip, and panties, all borrowed from my mother. No wig and no makeup, so the effect was a little disappointing. I'd been partially dressing for many years before that, but this was the first time I dressed fully.

  12. #37
    Exploring NEPA now Cheryl T's Avatar
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    It was Mom's.
    I have no idea how it looked on me, how I looked in it. All I remember is how wonderful it felt to wear a dress. Of course I had her lingerie on beneath it so that was wonderful too.
    I don't wear women's clothes, I wear MY clothes !

  13. #38
    Aspiring Member Robbiegirl's Avatar
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    Quote Originally Posted by Kirsty2907 View Post
    Robbiegirl
    There is a line......
    And you have crossed it ��

    Only kidding��
    No but I did used to fancy Chris Evert and Jennifer Capriari
    Here is the great Chris Evert in her cute dress and ruffled undies

    Tennis Classics.jpg

  14. #39
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    My first time in a dress was one of my mums, it was one of her favourites and she looked really nice in it, it was white with zipper up the back (that was a challenge first time), short cap sleeves and some lace round the neck, it felt amazing, I guess I was about 12yo by then, I had been wearing panties and bra's, plus I used to wear one of my mums nighties, but wow a dress, that felt like a step up and it was

    That was where my love affair with dresses began I guess and I still get that wow feeling when I wear one now, some 50 years later

  15. #40
    Member Rosemary+'s Avatar
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    The first time I wore a dress, is a memory I?ll never loose it was the most wonderful feeling.
    I was about 4 years old and I hadn?t started school. I was playing in my grandmothers bedroom and I saw this beautiful yellow dress �� hanging in her wardrobe. For some unknown reason I just had to try that dress on. When I slipped it on, I felt amazing, it felt right, it felt like I should always wear dresses. After that first time, when my family visited Nan?s I would make a bee line for her wardrobe and and try on one of her dresses. Eventually my parents worked out what I was doing, I can vaguely remember my father explaining to me why boys don?t wear dresses.
    What amazes me to this day is, My memory of wearing that yellow dress is so much clearer in my mind than the talking to from my father

  16. #41
    Gold Member Lana Mae's Avatar
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    My first dress was put on just a few years ago! It was a claret knit below the knee! Somewhat frumpish! BUT, the freedom and joy it brought is beyond words! Hugs Lana Mae
    Life is worth living!
    "Foxy lady! You look so good!!" Jimi Hendrix

  17. #42
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    I did not know this until a few years ago, but when I was a baby, my mother would dress me up as a girl and pretend I was one. She really wanted a baby girl and this was long before anyone knew the sex of a child before it was born.

    She ended up with three boys and no girls so she would sew dresses for her nieces. She would make me try them on so she could see how the fit and mark the hem. I remember protesting, but in hindsight, I might have enjoyed it. This was before I was five years old.
    Krisi

  18. #43
    Senior Member BrendaPDX's Avatar
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    I have posted this before, in fact I went back and found it. LOL Here I go again... Early high school, I was at the Salvation Army thrift store, I ran across a dress and just had to have it! I paid for with shaking hands, and tried it on that night. Of course it had to fit perfectly! I remember the side zipper, I had never seen one before, but when I sipped it it pulled the dress around me and fit perfectly! I was stunned at the pretty girl in the mirror looking back at me. A girl like "that" would never date a boy like me. I must have stood there an hour... The die was cast!!!

  19. #44
    Aspiring Member Rayleen's Avatar
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    first time was my wifes hot pants in the 70s. its started me do buy my own.
    Wanting something is a fantasy which on a long time period clouds your mind and makes you think you need it.

    Rayleen

  20. #45
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    Well let's see.... the very first time I wore a dress, it was actually a cosplay outfit of Princess Peach, so I don't think it was a real dress. I knew I was a guy and that I shouldn't be doing these things, but I just couldn't help myself. I felt really girly and feminine, and just felt like a princess in general. As I wore it more often, I started to wish I could actually be a princess, and then wondered what my life would be like if I were Princess Peach. Those feelings have not gone away even today, although I'm not really interested in being a princess that much anymore, preferring to wear other women's clothes.
    The first time I put on a real dress, it was from an online crossdresser store. It felt good to wear something that a woman would wear and not just cosplay. There was one problem.... I had no set of breast forms. So when I looked in the mirror while wearing my first dress, I saw a flat-chested woman looking back at me. I liked the look very much and was happy, but I had to have the breast forms so I could have the appearance of a woman with breasts. Well, when I got my breast forms and put the dress on a second time, it was a hundred times better, and I loved the dress even more than before.

  21. #46
    Junior Member sherlynn's Avatar
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    I don't remember the exact age but it was my pre-teen years. My mom was a seamstress and quite often she would make dresses for my cousin who was about my age. My mom didn't have a dress form so she would make me wear the dress while she worked on hemming the dress or taking in the waist and what nots. It wasn't always pleasant as I would get stabbed by those pesky dressmaker pins quite often.

  22. #47
    Aspiring Member Robbiegirl's Avatar
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    Quote Originally Posted by sherlynn View Post
    I don't remember the exact age but it was my pre-teen years. My mom was a seamstress and quite often she would make dresses for my cousin who was about my age. My mom didn't have a dress form so she would make me wear the dress while she worked on hemming the dress or taking in the waist and what nots. It wasn't always pleasant as I would get stabbed by those pesky dressmaker pins quite often.
    Did you ever see your cousin in one of the Party dresses your mom made her ? I would think that would be a bit ackward but funny ?

  23. #48
    tiptoeing thru the tulips ellbee's Avatar
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    I honestly have no idea.


    But one that sticks out to me?

    I must have been around 16. Not to brag, but I had a very hot & fit GF at the time.

    Christmas was coming up. She was a girly-girl, with a slight tomboy touch. And she was *very* much into fashion & all that. She also enjoyed shopping at those "hot-GG" clothing stores at the mall.


    Anyway, we went into one of her favorites, so she could pick out one of her gifts. Don't even remember the name, as they're always changing all the time & it was a long time ago.

    OMG, was I in heaven!

    Completely surrounded by all these young, hot GG's shopping for all these hot-GG clothes, with girly music playing throughout the store. I was also the only guy in there, ha!


    She picked out some things, then modeled them for me. I wasn't *totally* in the dressing room area when she did, but I was probably a bit too far in? Hey, she did coax me to come closer, after all. And luckily, none of the other GG's seemed to mind... Being a young pretty-boy definitely had some benefits, LOL.


    So, she settled upon a tight & slinky long-sleeve low-cut mini-dress in a gorgeous black stretch velvet. And she looked absolutely amazing in it!

    I paid for it, she grabbed the (girly) bag, and out we went.


    Of course, the only issue? It wasn't quite Christmas just yet. So, I told she would have to wait for her gift -- and I would hold onto the dress in the meantime.


    Suffice it to say? I wore that thing a *lot*!

    Not exactly proud of that, honestly. But, I was a young & horny CD'er. Besides, technically it wasn't hers just yet... So, I forgive myself.


    Sadly, Christmas came all too quickly, and I finally had to cough up the goods.

    Fortunately, she looked way better in it than me!


    She wore it for a few occasions. I remember one time, she *really* got all dolled-up with the hair & make-up & heels & what-not. When she was ready, she came down the stairs... OMG, the bright-red face of her father!

    Of course, little did they all know, that I had worn that dress first.

  24. #49
    Aspiring Member Georgina's Avatar
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    I tried on my first dress in my early teens. For the first 5 or so years of my interest I just wore lingerie. Back then my drive was mainly visual. I adored the way slips looked while wearing and I really did not wish to cover them up. Eventually I took the plunge when my mother's dresses fitted better. I was hooked immediately even though the dress was not a perfect fit.. Years later, in the 90s, my mother got a new dress that was a perfect fit and felt so lovely to wear. The joy and excitement that that dress generated was immense. I wore it to death and much more than my mother did. I still have that dress today, a little the worse for wear, but the memories it helps relive are magic.

  25. #50
    Junior Member Janet Devon's Avatar
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    My first outfit was a jumper but looked a lot like a dress. I was about 12 or 13 and my mom and sister helped me dress and walk and look like a girl for a contest. I won first place and had several guys looking at me like they seriously wanted some of that. It was written in the paper that I had to turn down dates but that was not true. My first dress was a blue formal bridesmaid's dress that my wife wore at her girlfriend's wedding. I was probably about 20 at the time. I still have that dress but I have outgrown it. I don't have the same wife either, out gown her as well.

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

    Geena,
    I was going to say that I can't see fitting that many dresses in my closet but then I started counting. I have maybe 10 or 11. I have a lot of blouses and a few skirts. For some reason, I am attached to one black skirt that fits perfectly and goes with almost any blouse.

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