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

  1. #1
    Member Robbiegirl's Avatar
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    Can you remember the first time you put on a dress ? What it looked like, whose dress

    It was and maybe most importantly how you looked and felt wearing it ?

    Growing up in the late 50s girls wore dresses almost daily but their party dresses were so fem. Around 7 I tried on my older sisters old party dress

    a Very short yellow chiffon dress with puff sleeves . I couldn't believe how I just looked like a girl in it, twirling about ! LOL I was hooked !

  2. #2
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    I did not have an older sister or female cousins. I was all boy until puberty hit. The only access to female clothing was my mother's clothing. The first dress I tried on was one of her summer dresses. Yes, it was from the 1950's and 1960's. A pretty floral dress with a wide sweeping hem. I was a real skinny kid so I did fit into it for awhile. It had a side zipper. That was the time period in my life of self loathing, self hatred of what I was doing. I outgrew her clothing so raiding her clothes ended. It wasn't until ten year later that I bought a dress to wear when my wife was visiting her family across the country. I pretty much got the same reaction and tossed it before she came back from her trip. Still a lot of self loathing. It wasn't until I gained self acceptance, and, stopped looking for validation from my wife that I started expanding my wardrobe.

  3. #3
    Princess Candice candykowal's Avatar
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    I suppose dressing in my closet Mom shared with me as all her small fitting clothes were stored in my closet.
    There were so many of those June Cleaver outfits in there, not one come to mind.
    The one dress I could call my own does come to mind as I put up such a tantrum to have one....
    ...you see, I fell in love with the confirmation dresses the girls wore in my Catholic grade school that I begged Mom to buy me something like that.
    So, for all I went thru, in the trials of being a femme teen, she bought me my first dress.
    It was a Madonna like, White Lace Ruffles Dress, laid on my bed with white Buster Brown Mary Jane patent leather shoes at the foot of the bed.
    Later that week, I also got a hand me down clutch, costume pearl necklace and bracelet, and some hair barrettes.
    You forget the ones you wore until you finally wear a dress you can call your very own!
    Candice Coleen Kowal ....all my friends call me Candy!

  4. #4
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    Think I was about 10
    Everyone had gone out, don?t remember why I done it or if I?d been thinking about it for a while, but slipped into my sister school dress.
    It was green and rather standard issue type thing..
    but that was the start

  5. #5
    Member Lori Ann Westlake's Avatar
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    Yes, I do remember. It was my mother's dress, in pale blue wool, fairly close fitting with three-quarter sleeves and a zipper up the back. I was already in full women's underwear when I put the dress on. I felt good in a bra, girdle, nylons and panties, with a white full length slip. I guess my mother's shoes fitted me too at the time. I slipped the dress over my head, pulled it down over my hips, and I think I had a little difficulty getting it zipped up behind me, which was not surprising. But once I had it zipped up around me, I felt (naturally enough) that the dress "completed" me. I felt deliciously "enclosed" in the dress, as if I were somehow "locked into" femininity. Though I had no wig, I probably didn't look too bad in the mirror. Anyway it was an exciting experience.
    Last edited by Lori Ann Westlake; 03-13-2021 at 02:24 PM. Reason: typo

  6. #6
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    As a preteen, I had access to my church after school and on weekends. Except all day Sundays and on Wednesday evenings, there was rarely anyone there. I walked to school. In those days, as long as I showed up at home by dark, no one cared.

    From time to time, the church had rummage sales. They stashed the leftovers in a closet in the basement before sending them to charity in the big city. I raided the leftovers. High fashion they were not. It was mostly old clothes from the 40s and 50s. But it was fun to dress up and I fit many of them.

    That is where I found my first dress, an emerald colored midi length number in a WW2 era style made of a heavy satin material. I found stockings and cheap accessories but there were never shoes or under garments. I must have been quite a sight but no one ever saw me.

  7. #7
    Aspiring Member kayegirl's Avatar
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    Aged 13, and it was my older sister's dress, home alone I crept into her bedroom. An olive green, with a flared skirt that needed a petticoat. Looked a lot better than it sounds, and with a white cardigan, knee high white socks and some light tan sandals, it was my first time fully dressed as a girl. Also my epiphany, from that day onwards I so wanted to be the girl that I saw in the mirror.

  8. #8
    Senior Member Christie ann's Avatar
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    My mom was an enthusiastic square dancer. All those big skirts and bigger petticoats. My middle school years were full of scanning the special square dance closet in those few minutes after school before anyone else came home. My parents always asked why the curtains were always closed in the afternoon. As only a 12 year old can say...”oh, are they, I didn’t notice”

  9. #9
    Aspiring Member jacques's Avatar
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    hello Robbie,
    the first dress I wore was my own and it was probably just a few years ago. Until then I had worn skirts and tops.
    luv J

  10. #10
    Member DanielleCD's Avatar
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    I don't remember the first time but I wear a dress whenever I get dressed now. Beyond the panties, bra and forms... a dress completes the wardrobe for me now.

  11. #11
    AKA Lexi sometimes_miss's Avatar
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    I was four; my mom routinely got my sister ready for school, picking out her outfit, fixing her hair, every morning. This took quite a while, so, feeling ignored every day, I went to my sister's room and took one of her dresses and put it on, went up to my mom and sister, and proudly said, 'I'm ready to go to school, too!'. Of course mom would have none of that, and got me changed back to my boy clothes, and we walked my sister to school.
    When we came home, mom asked me if I really wanted to wear the dress, but said it in such a manner to imply that my answer should be no, so that's what I said. I hadn't seen myself in the mirror, so I don't know exactly what I looked like.
    Some causes of crossdressing you've probably never even considered: My TG biography at:http://www.crossdressers.com/forums/...=1#post1490560
    There's an addendum at post # 82 on that thread, too. It's about a ten minute read.
    Why don't we understand our desire to dress, behave and feel like a girl? Because from childhood, boys are told that the worst possible thing we can be, is a sissy. This feeling is so ingrained into our psyche, that we will suppress any thoughts that connect us to being or wanting to be feminine, even to the point of creating separate personalities to assign those female feelings into.

  12. #12
    Aspiring Member Geena75's Avatar
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    1975. My dad had bought the leftovers of a group yard sale to sell at our house. There was a short, dark purple dress (barely covered my rear). Short sleeved with elastic in the ends of the sleeves, thin white lace trim around the chest area, and zipped up the back. I remember rigging up a wire to attach to the zipper so I could get it zipped up all the way. Wore it with an old pair of pantyhose my sister discarded. I remember once the wire came off, and I panicked at how I was going to get out of it. Also remember diving in bed and covering up when I thought my parents had come home. I was at my full height then, but a lot less bulky or muscular than now.

  13. #13
    CD ROM Bluesman's Avatar
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    I was in my mid-30s before I put on my first dress, despite having worn panties, bras, nightgowns, other lingerie off and on since my early teens. Didn't have any sister's clothes to try on. My first dress was a sleeveless white knit sweater dress that I bought on impulse off the rack during my lunch hour from work. I was living alone at the time and couldn't wait to get home to try it on. And it fit! That in itself was a revelation as I am 6'5" (but slender). It was stretchy and form-fitting and felt very sexy. I didn't have it for very long; I purged when my girlfriend and future wife moved in with me. Still wish I had that dress! 40 years later I have 14 dresses not counting the 6 or 7 that I retired for various reasons (fit, style) over the years. Wearing one of my favorites now, but missing that white sweater dress. No more purging though!

  14. #14
    Gold Member Alice Torn's Avatar
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    I was around age 13 or 14, my sister's sleeveless courderoy green one. Was on cloud nine, but sure felt guilty after.
    IT TAKES A REAL DRESS TO WEAR A MAN.

  15. #15
    Aspiring Member ShelbyDawn's Avatar
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    I don't remember my first, I was probably five or six and was trying on lots of my sister's stuff.

    The first one I remember was a formal, one of four my mom left in the garage after my sisters chose the ones they were going to wear and the only one I remember.
    I was fifteen, tall and skinny and it fit like a dream, taffeta with a built in petticoat, crinoline or tulle, probably, with sequins all over the bodice.

    I don't think I have ever felt as pretty as I did that day. I must have danced around the garage for an hour before I finally tried to take it off, of course the zipper stuck and it took me another twenty minutes to get out of that. I was just lucky no one walked in on me.
    I do remember many subsequent trips out to the garage and trying on all of the dresses, but the green one is the one I remember.
    I am Me and Me is OK!



    Shelby

  16. #16
    Miss Conception Karren Hutton's Avatar
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    When I was 8 or 9.... the gang of girls on our block made up a game called... Catch a Boy and put a Dress on Him.... and I know I was not the slowest boy on the block but for some strange reason I got caught more than anyone else... Ohh Darn! The dress was an old dark colored, maybe blue, velvet sleeveless dress... and it smelled old like one of the girls grandmothers dress, I am guessing. And it felt amazing on! All the girls ooooed and aaahhed! I felt like a princess and I wish I could thank those girls!!

  17. #17
    Aspiring Member DanielleDubois's Avatar
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    I was 10 or 11 and I found a beautiful angora sweater dress along with a corset style full length girdle in a cedar chest in my parent’s basement. I still wonder why those two particular items were saved in a basically empty cedar chest along with some random papers. But a very young Danielle did have some fun with them and the rest as they say is history.

  18. #18
    Oh to be an English Rose Jane G's Avatar
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    I can't actually recall the first time.

  19. #19
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    I was 9 I think, and it was my mom's bra and panties then moved to my sister's wardrobe. Felt weird at the time but I realized it was pretty nice and comfortable.

  20. #20
    Silver Member Kay J's Avatar
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    I was 10 also it was at a friends house one of his sisters dress a blue dress with sheer sleeves and wore a petticoat and stockings with it. My friend had to try one on also we both hit puberty that day to!

  21. #21
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    Robbie,
    I do remember at about 9 trying on my sisters full layered petticoat for the first time , it did make my head spin . I still feel we were lucky at that time as we had the full cotton dresses and skirts worn with a full petticoat or nice full slip and then we had the start of mini skirts , I couldn't wait to slip into a mini dress of my sister's .

  22. #22
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    First time that I put on a dress was when I was about 20 and was trying it on in a charity shop.

  23. #23
    Aspiring Member MonicaPVD's Avatar
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    The first time I tried on a dress I was 15 or so. It was a small stretchy red number and very short. Until that point, I had stuck to hose and intimates. It was probably the most exciting thing I had done to date. A few weeks later I had a friend over after school. We were playing video games and we started talking about the upcoming Halloween party at school. I brought this up because I was looking for an excuse to dress in front of anybody. I told him that I was going to dress up like a hot girl, he laughed and I said, wanna see? It was scary and such a rush to walk back into my room in a dress and heels and see his reaction. I think that was a defining moment in my life.

  24. #24
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    Sometime around 5th grade I wore a dress for my schools Halloween party that is my earliest memory. One of the most memorable dresses I wore was in my early twenty?s and married my wife had borrowed a dress from her sister for a holiday work party but it was a couple sizes to big for her well the first time I was home alone I put on a pair of my wife?s panties and pantyhose then came the dress it was the early 80s the dress had puffy sleeves and a full skirt just above the knee. What I remember most is that was the first dress I wore as an adult that I could zip up and fit me perfect it was an incredible feeling I will never forget.

  25. #25
    Aspiring Member kellyanne's Avatar
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    In my 20s but the first forays into dresses were all too small, then I hit on a 3 part wedding dress and it fit great.

    Have a few dresses but am generally a blouse and skirt girl.

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