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Thread: How did it start for you?

  1. #51
    Aspiring Member Karmen's Avatar
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    I don't know why, but as far back I can remember, I was always drawn to female clothes and shoes. I never felt as a woman hidden in a male body, but always wanted to wear female clothes. Need for makeup and wigs came much later, when I wanted to go outside and wanted to look as closely as possible as a woman.

  2. #52
    Aspiring Member Bea_'s Avatar
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    I have vague memories of my older sister and a friend dressing me as a girl once when i was maybe 4 years old. I'm not thinking that had any major impact though. Not a trigger for me.

    As an adolescent, my mom and the same older sister would leave bras hanging in the bathroom. When the testosterone kicked in at age 11 or 12, I'd put one on just to have something feminine to am the hormones at. I never really associated the bras with my identity. Still not a trigger.

    I grew up in tighty-whitey's and when I began buying my own underwear, I'd always look for men's bikinis. I'd always check the underwear section when I went to any department or clothing store to see if there were something 'different'. There never was.

    About ten years ago, I tried on a couple of pairs of my wife's cuter panties and decided that THAT's what I'd been looking for in the men's underwear department. Shortly after that I bought 2 or 3 pairs of panties from a dollar store, not knowing what size to get and buying a couple of sizes too small.

    Shortly after that I 'confessed' to my wife that i'd like to wear panties and we ended up at Kohl's one afternoon. She had me wander the store while she chose some items that she thought she could handle. She chose well. We left the store with probably a dozen pairs of panties, mostly bikinis, but also some really nice thongs. Within the next year or so I hit the first hundred pair.

    I expressed interest in leggings and got 'approved'. Then some tops. She shocked me by holding up a dress that she thought I might like on one trip out. I don't think I'd ever mentioned that I'd like one before that. On another trip she picked out a really cute sundress.

    I retired last year and spend most days that we don't have a big agenda, at home in something femme. No forms. No makeup. Full beard. But, me in a dress, or skirt and top, or leggings or...

  3. #53
    Member chrissietoo's Avatar
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    Fascinating and sexy thread! I don't know what I was doing at age 5, but I do remember I was very interested in girls and their clothes. Out of the blue I asked my mom if I could be a girl for Halloween, and she put together a costume for me...I was in bliss! I remember also the girls as they first were wearing bras, and the nice fuzz on their legs, which then disappeared. I noticed everything--soft sweaters, crisp blouses, silky hair, and did I mention bras?

    I was just growing a couple of pubic hairs when I would spy on an older girl in an apartment across from ours, because once I saw her in her bra. One morning I saw her hanging a bra on the line down at the laundry, and I was compelled to take it. I put it on a couple of times, but it didn't fit at all, but I kept it as a prize possession. Puberty is a big blur, and then at 16 my girlfriend left her bikini in my car, and I was seized with the compulsion to bring it to my room. When I put it on late that night, a jolt of electricity shot through me, as well as a huge sexual rush. If I wasn't gently hooked before, I was that night!

  4. #54
    Member laura.lapinski's Avatar
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    Chrissietoo Mine started with a bathing suit too. A one piece. I felt the same as you stated when I put it on an looked in the mirror. I liked the way it felt on my body, hugging and snug. I was about 13, but I had some thoughts in years before that.

  5. #55
    Junior Member Manasi's Avatar
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    When I was about 10, I envied girls at school, they got to wear dresses, have long hair, and wear jewelry and later makeup. I started trying on my mum’s clothes when I was at home alone. I started buying my own clothes when I moved to the US to study, and only started coming out to friends about 3-4 years ago.

    xoxo,

    — Manasi

  6. #56
    Member Dana3's Avatar
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    Ever since I can remember as a young boy 👦 I've ALWAYS have been drawn to, towards, enthralled, fascinated with girls, women, femininity, and all things associated with same.

    When I was younger, prior to going to school 🎓 around 3ish to 4 or so? My oldest Sister would play with a neighborhood 🙋 girlfriend.

    They wouldn't let me join in only if I dressed as a girl also. Since what they were playing was for girls 👯 only.

    About this time, we had a 16-year-old girl 💁 cousin. Puberty being what it was, I suppose, she would molest me, until once she hurt 🤕 me and I threatened to tell my Moma. 😟

    I had no awareness of the differences between 👶 boys and girls 👩 other than the obvious
    external ones. At my age, I never able to connect the dots.

    Later I would enjoy looking at and through the various catalogs, Sears & Roebucks, JC Penny, Rommans, Lane Bryant.

    Later I became fascinated with lingerie, and Fredricks of Hollywood ads that I would come across in various magazines.

    My parents 👨*👩*👧 separated and divorced. My two ✌️ sisters went to live with my Mother in another state, I stayed behind and lived my Grandparents on my Dad's side of the the family.

    Along about the time I was in the seventh grade, my then 16 year old sister came to stay with my Dad and I.

    I distinctly remember "To understand girls, be a girl!". And I tried on a pair of my sisters underpants.

    ,🤤 😲 🙂 🙃 😍 😘 😍

    Things progressed as they say from there.

  7. #57
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    I remember first trying on my mom's pantyhose/nylons when I was around 5 or so. Do not remember trying on anything else fem after that. When I was about 21-22ish, my gf at the time decided to dress me up for one of her friend's Halloween party since I had long, natural wavy hair at the time. She helped me shaved my legs at the time and picked out a few outfits at a thrift store. I was hesitant at first at the idea, but a rush fell over me when I first tried the items on and she did my makeup to make me look fully passable. The rush intensified when I caught a few guys checking me out at that party. For full disclosure, her friend who hosted the party was gay and there were a lot of gay guys there. I dressed up quite a few times for my then-gf.

  8. #58
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    When I was eleven a girl I was completely infatuated with was sent away to boarding school. The school was just for girls. I imagined dressing as a girl so I could be with her. It was her who made me excited, not the thought of being dressed as a girl. I have no idea if that was what set me off. My mother was always very fastidious about what she wore and made comments about what women on television were wearing and I suppose deep down I am seeking her approval when I dress up as I like to put a really good outfit together even with the right accessories. To this day what I like to achieve is an outfit that looks good not that makes me feel like a woman - I don't - I feel like a man no matter what I wear and identify only as a man. So I only speculate about why I do this. As a grown-up I formed a relationship with a woman who had gone to the same school as the 11-year old I worshipped (pure coincidence). I am not sure if it is a hobby or an obsession and it is possibly significant that my younger sister is as obsessed with women's clothes as I am and we both have far more than any normal person would.

  9. #59
    New Member JennaDcd's Avatar
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    Not sure how old I was, maybe 6 or 7, but I remember seeing my mom's silk panties in the clothes basket and getting aroused. From that point on I was hooked. Whether it was my mom's, my sister's, or an aunt's when we'd visit, I spent my youth sneaking off with their silk or satin panties and trying them on. Never got caught, thankfully! Occasionally I'd also sneak off with their bras, stockings and any other lingerie I was in the mood to try on. Now, in my early 40s, I have completely accepted that it's who I am and will likely never go away.

    One thing I have realized though, is that for me, it's purely sexual at this point. I only dress when I'm aroused ... or dress to get aroused. Never just to relax or because I feel like a female trapped in a man's body.

  10. #60
    Aspiring Member Lacey New's Avatar
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    I started in my early teens. Back then the girls in junior high school wore skirts and would occasionally provide an intended glimpse of panties. I was also fascinated by seeing bra straps on budding breasts. So I would look at the panties and the bras and would imagine the wonderful things underneath them. Well, Mom and a sister a year younger provided plenty of lingerie in the hamper and one day just out of curiosity I decided to see what it felt like. The fabric of the panties was soft and silky and exciting. I had a few moments so I put on a pair and you can imagine what happened. Well, not only was it exciting but it was addicting. If panties were great, panties and a bra were even better. Then stockings, slips and any other lingerie I could find. Pretty much the rest is history.

  11. #61
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    I was around 10 when some one was watching the weather channel, and I noticed the suits the ladys were wearing. For some reason I wished I could wear them. Now at 35 years old. Im pretty sure that is why I love female office attire, and it looks good on me. Compared to normal clothing. Like jeans, and a top. While I pretty munch wear womans clothing every day. I really wish I could wear office attire all day every day.

  12. #62
    Aspiring Member dana digs sweaters's Avatar
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    Quote Originally Posted by Ginger82 View Post
    Did you always feel more femme than male or did you start experimenting with crossdressing and it progressed from there? Obviously it doesn’t fall neatly into those two categories, they’re just examples of what I’m asking. But what’s your story…?
    Being the only boy with 5 sisters (3 older) , there was no how, no way that I wasn't going to end up wearing their clothes.
    Seeing Flip Wilson and Klinger from M*A*S*H* on a weekly basis dressed as a woman gave them plenty of ideas.
    Could also include Bugs Bunny, the 3 Stooges and Milton Berle reruns
    A lot of skits were done where I was in their clothes. Of course I never refused
    How could I when it was fun to me? Always funny to them also.
    Of course I experimented without them from age 7 on.

    once a boy puts on a dress and heels.jpg

  13. #63
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    Long ago, I slipped into my first pair of panties. They were purple with tiny white stars. The panties were a bikini cut made of soft cotton with a tiny lace trim along the waist. I felt excited and nervous as if I was doing something deliciously forbidden. My head was spinning. Around the same time, I paired the panties with a demi bra. It was lightly lined for a subtle lift and had underwire cups. It was probably made of nylon and spandex. I distinctly recall it was coconut white. The feeling was sublime!

    At some point during a hot summer evening of my (very) early teen life, when my parents were away, I did something really bold. I wore a complete feminine outfit while bike riding around in my neighbourhood. I had on a cap, bra, panties, denim short shorts, a thin t-shirt, and a flannel button up shirt tied about my waist. On my feet were sneakers. I walked into a convenience store and I purchased candy or a magazine; I forgot which exactly. But I do recall my heart was thundering the whole time!!

  14. #64
    Member HelpMe,Rhonda's Avatar
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    One of my earliest memories is putting on a pair of Mom's earrings, and some sort of big reaction happening.

    Later on it was putting on a dress she had for some big event, when I was somehow old enough to be home alone, and then it kept going and going and going.

  15. #65
    Nylons lover GeorgeA's Avatar
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    Re: post#10 NancySue.

    Nylons started my cross-dressing and are an essential part of my daily attire. Without nylons I'm not dressed.

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

    Starting age.

    Most posters said they were about 5 when they developed an interest in lingerie, etc. I think age of 5 is the transition point from being babies to pre-schoolers. Our curiosity develops and we start exploring the world around us. We start being independent and that includes varieties of clothing. I also was 5 when I tried to put nylons on. I wrote about it in my introductory message when I joined here.
    GeorgeA
    formerly Salerba

    "a miad" Man-in-a-Dress

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