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

  1. #51
    Member occdresser's Avatar
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    I was 12 or 13 and I didn?t have a Halloween costume so my sister said try on this dress, well I loved it but said I can?t wear that, greatest feeling ever, so I always checked her closet after that for more dresses
    [SIGPIC][/SIGPIC]

  2. #52
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    Hi Robbie , That was OH so many years ago , I am sure that it was an awesome feeling,

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  3. #53
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    I was older than most. I started very young with petticoats and slips, but didn't try a dress until I was about 30. When my wife (at the time) was away I tried her bra and a navy dress. Now I wear dresses about the house quite a bit, and love them.

  4. #54
    New Member UsuallyRick's Avatar
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    First time was very young (like 6?) my parents friends were over with their daughters.. we got into my older sisters dressup chest, they dolled up then went to town on me, like 3 princesses!! The parents had to check on us because we were being too quiet.. oops.. then before we got married my then girlfriend and I went to a Halloween party with her dad and stepmom,(they both were part people) we both dolled up as hookers and said we were lesbian hookers.. took til the end of the party before anyone realized I was a male😁🤣, the hostess loved it and said I would have won the first place had they known.. can't get enough dress wearing in my life now, but still only come fully out of the closet at Halloween.. wish my wife was more ok about it.. her ,our younger daughter ( 19) and I have fun checking out cute girly stuff and I say I would totally wear that..ha ha maybe she's more ok with it than I know??

  5. #55
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    I was maybe 13 years old, and found this dress in my mom's closet...a tight sleeveless thing with a high collar, that hit right at the knee. It was black and white, that's all I remember about how it looked. But I put on a pair of black tights and that dress, and a pair of her black pumps and...wow. It felt amazing, so completely different than jeans and tee shirts or whatever else I usually wore at the time. The feeling of the tights, the hug of the dress...it's strange to say but it felt comfortable. Of course I grew fast and it wasn't long before I couldn't get it zipped anymore and she eventually got rid of it anyway. To this day I have no idea how she ever fit into it, either, hah.

  6. #56
    Sallee Sallee's Avatar
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    Not sure it was the first but my guess is around 12 would sneak into the dirty cloths basket and try mother's dress on. If they were gone for a while would head to the closet and try those on. Kept it up for awhile and finally realized I had to stop so I moved away from New England to Colo because I am sure being a mtn man would cure me. After a few years settled in Denver and could buy my own dresses Frequented all the thrift stores in that city.
    [SIGPIC][/SIGPIC]Sallee

  7. #57
    Miss Judy Judy-Somthing's Avatar
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    At about 8, I remember the first outfit i wore because my sister took a photo.

    Been hooked ever since.
    "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.
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  8. #58
    New Member sherlynn's Avatar
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    As a matter of fact I have seen my cousin in a dress my mom made. It wasn't awkward since she didn't know but it did get a chuckle out of me knowing that I had worn her dress before she ever did.

    Quote Originally Posted by Robbiegirl View Post
    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 ?

  9. #59
    New Member samuktv's Avatar
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    My first time was amazing I only ever wear dresses now x

  10. #60
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    Robbie,
    I've just read your comment on wearing a tennis dress , I played tennis at school and then later joined a tennis club , I haven't played in years but I'm considering taking it up again as I've found someone who runs a group for more mature players . So I've been checking out tennis dresses , can't find any with frilly panties most now come with shorts .

  11. #61
    Member Robbiegirl's Avatar
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    Quote Originally Posted by Teresa View Post
    Robbie,
    I've just read your comment on wearing a tennis dress , I played tennis at school and then later joined a tennis club , I haven't played in years but I'm considering taking it up again as I've found someone who runs a group for more mature players . So I've been checking out tennis dresses , can't find any with frilly panties most now come with shorts .
    Teresa you need to be a fashion starter and bring back the frilly tennis panty ! LOL

  12. #62
    Aspiring Member SaraLin's Avatar
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    The first dress I can specifically remember, though it might not have been the very first...


    I was about four or five. The dress was my grandmother's. It was a plain, rather frumpy, cotton house dress. I don't remember the pattern or the color, but probably a drab green or blue. It was a thousand sizes too big for me - like wearing a tent. My grandmother had to put a belt around my waist and hike up a lot of the skirt material under it to keep me from tripping over it - giving it sort of a double-layered skirt effect.

    She would do this if I slept over at her house, since she didn't have PJ's for me.
    I must have looked ridiculous.

    But I was in heaven. For even a few brief moments I was allowed to "be" a girl.

    I have a couple thoughts about these times.
    I don't think that this "started" anything. I already knew I was supposed to have been girl.
    I also remember being embarrassed by it. Even back that young, I'd learned that "boys don't wear dresses" and despite what I felt, I knew that I'd been born as a boy.
    I guess my journey of self-doubt and shame started very early.

  13. #63
    Oh my god, I'm a girl! jazmine's Avatar
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    I'm pretty sure I was in second grade. It was my Mom's dress when she was a little girl when she first received the sacrament of holy communion. It was really frilly and "poofy". Lol! I remember always being mesmerized by it. My childhood home was a bungalow and I had the entire upstairs as a bedroom. One whole side of the hallway upstairs next to the staircase was closets for the entire family. So I pretty much had access to everybody's clothing. Why my mom still had the dress I do not know. One day, for whatever reason, I just decided to try it on. That's the day I found out what heaven is. She also had her eight grade graduation dress in the closet, which was a light pink & equally as cool. When I grew into it, I also would wear it. Why she kept these relics, I do not know, but it changed my life. I love my family. Cool peeps! I got a little something cool from everyone. My dad being a craftsman, loving old cars which led to my love for old Mopars. My uncle being into music and playing guitar, which led to my career. My mom was super cool. Taught me how to be a good human, be me, and chase my dreams. I got "womanhood" from her. ....at least as close as I could get to it.......
    So I like dressing like girl. BIG DEAL!

  14. #64
    Member Kiwi Primrose's Avatar
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    I was still at high school and was at my girl friend's house when she was dressmaking. It was a dress for herself and she asked me to try it on so she could measure it and mark the hem lines.
    Of course I agreed and and she realised I enjoyed it We have been married for over 60 years and she has always helped with my wardrobe.

  15. #65
    New Member MilenaSometimes190's Avatar
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    High school and trying som eof my mom's dresses. Then yearls later bought my own.

  16. #66
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    For extra family income my mother did sewing and alterations. At around 12-13 years old I was drafted to be the dress dummy. I got to wear a lot of fun dresses and skirts in my size. Unfortunately I showed a little too much interest in wearing the clothes and was soon replaced with a dress form from a second hand store. My bubble was temporarily popped.

  17. #67
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    I never considered my mom's or sister's clothes as anything to be desired. They never had a style that seemed attractive. Very plain.

    Moving on to my marriage, it was a couple of decades before I ever felt an inclination to try any of her things on. When I did try on a couple of her cuter items, it just didn't do much for me. Even though i did try on various items out of curiosity, I would never define myself as a crossdresser at that time. To answer the specific question from the OP, to the best of my memory, i tried on a white dress that my wife had only worn once or twice. It was not fitted at all. I didn't hate it on me, but, at that time, it didn't bring any real desire out. It was only curiosity that was totally satisfied and not repeated for years.

    After some major trauma over several years in my fifties, I developed a very clear inclination to want to wear things I'd never even considered as an option or even desirable up until then. When I began experimenting, I found a sense of 'rightness' and a sense of strength that still seems unfathomable. Now, half of my wardrobe is from the woman's department and, since I've retired, well over half of my time at home is spent in things from the femme part of my closet.

  18. #68
    Just finding my way.... StaceyJane's Avatar
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    It's been so long I don't even remember how old I was. It was one of my mom's dresses I tried on and the feeling of of wearing a dress was so wonderful.
    Stacey

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  19. #69
    Member Jazzy Jaz's Avatar
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    I don?t remember which was the first dress as I took several dresses from my sister but they were all lovely and made me feel amazing. I started dressing when I was 11 and the first item I wore was a pair of hot pink panties, from there I quickly ended up having bras, panties, stockings, garter belt, skirts, dresses, swim wear, lipstick, heels, a wig, and purses.

  20. #70
    Junior Member AndieB's Avatar
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    Honestly, I have no idea what age it was. I'm guessing it could have been around 4 or 5 years old. I remember my parents catching me wearing one of my mom's black lace nighties in a back den. It was super cute and probably felt like a lace dress of some sort since I was still small. I remember my dad saying "we caught a princess" and after that I know I got into my mom's stuff more often. Once I was big enough I started trying on her skirts and dresses, especially in middle school. I would get off the bus while my parents were at work and went straight to my mom's things where I would put on some nylons, a cute slip, a blouse or a sweater, and one of her many skirts. I can't imagine she didn't know because her pantyhose must have been stretched out. Unfortunately I wasted many years in college not dressing as much, but once I hit 25 or so it started again. Ever since then if you had to make a graph of my time versus en femme desires it would look similar to the Nasdaq for the past 10 years -- straight up and no sign of stopping, at least I hope...

  21. #71
    Member DanielleCD's Avatar
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    I don't remember the first time in a dress. When I first started dressing, around 14 years old, it was about lingerie. Panties and bras and stockings. Stayed that way for many years but somewhere along the line I started with skirts and graduated to dresses and heels. Now I'm not complete unless it's it's the full outfit... Have a new dress and underwear to try out today.. with new matching heels. If I get brave enough I'll post some pics in the gallery forum.

  22. #72
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    When my roommate was out for a few days for christmas, I tried on her blue robe dress, and one of her sport bras (which I stuffed with some socks). She was a bit on the thick side, so the dress and bra fit me great. It felt ...amazing! Never before had I done something like this and I was hooked. I was 28.

    At this time, I remember that an older roommate had moved out and some heels had been left behind in the basement, so I tried them on also. They were like 1.5 sizes too small, but I forced them on my feet, and, though each step hurt, it was euphoric. Shaved the legs, and the feeling of the dress and the look of the heels was like a totally different person.

    I had been questioning myself at the time, so this definitely helped me discover more of me. Still don't do it very often, but this was the time I found Christinne.

  23. #73
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    I was 8. We, my aunt and a cousin (boy), were traveling to a resort.
    Mom bought a piece for another of my cousins (girl) who stayed at home. By some reason I decided that this was a nightgown bought for me and demanded to try it. Mom eventually gave up and allowed me to model that nightgown(?) in front of everybody. After a few minutes, I remember, I proclaimed "it is very comfortable". But since it was a "nightgown" at it was still a daytime, I was quickly changed to regular clothes and I never saw that nightgown again and this event was never mentioned in the family. Years later, the cousin(m) who definitely was present at the time could not remember that it ever happened.
    I think, for me it was also kind of unmemorable experience. Since my second real dress come many years later (in late teens), stolen from mom's closet and I understood what I was doing.

  24. #74
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    Good question hmm, first dress was from a bundle of old clothes my mother left in the cupboard. First was a jean skirt but dress was blue and huge on me .

    What an impact.

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    i think any age is the right age, never regret what we missed but what we do now is so important.

  25. #75
    Silver Member darla_g's Avatar
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    i think i was 12 or 13 in middle school . I was home alone so i put on one of my mom's dresses but a full body shaper first. All remembering the exact way these things were situated in the drawers or closet. My mom had a wig in a wig case so of course i put that on as well. and i remember having one of those huge 50 eye shadow assortments as well. It was quite a feeling and escalated too quickly to no good.

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