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Thread: I'll always remember the first time that I........

  1. #51
    Member Megan b's Avatar
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    Two first come to mind for me. One is right after I bought my first wig. I began to transform myself as far as I could go. Then my wife did my makeup and applied my wig. It was the first time that could see a woman looking back from the mirror at me. I almost started the cry but I didn't want too mess anything up. It was awesome. The second thing that stands out too me is the first time I ever went out as Megan by myself. I went out on a Sunday night after church. Nice top, skirt, hose and heels. All it was, was just a trip to wal-mart. Scariest thing and funnest thing I had ever done. I thought everyone could/would look at me and just know but I did it anyway and just loved it. I was hooked after that although it would be about three years before I would do it again. Now it's no big deal I do all the time but I still remember with fondness that first time out.
    Last edited by Megan b; 06-12-2016 at 03:42 PM.

  2. #52
    Miss Judy Judy-Somthing's Avatar
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    I've been cross-dressing for 50 years and when the internet came around I like most looked at nude and non-nude photos of women.

    Even know I love dressing up as a women I stayed far away from anything related to cross-dressing, I'm not sure why!

    But last December I felt I needed to improve my makeup skills so I felt I needed to see what other cross-dressers were doing.

    That's when I found this site and I'm glad I joined!
    Last edited by Judy-Somthing; 06-12-2016 at 04:47 PM. Reason: TYPO
    "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?

  3. #53
    Aspiring Member
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    the first time I put one pantyhose. The best thing ever. One of my favorite things about dressing to this day.
    Also the first time I bought a bra, thought my heart beat could be heard by any one within 50 feet of me.
    Sara

  4. #54
    Hose & Heel Loving Divia. Lee Andrews's Avatar
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    Two milestones for me. First was being a young fella, looking at all my moms bra's, slips, panties and hose and having an unreal desire to try them on. Fought it for weeks but finally caved and here I am today.
    Second was the Internet, with which I found out I wasn't alone. As a kid I thought only gay people did this but I wasn't , so why did I? Still don't understand why but I have come to grips with it. I was pretty messed up trying to cope. Thank god for Al Gore or I'd still be messed up.

  5. #55
    Senior Member Lori Kurtz's Avatar
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    Quote Originally Posted by Lee Andrews View Post
    Thank god for Al Gore or I'd still be messed up.)
    Huh? Do you know something about Al Gore that I don't? You've got me curious ... Am I the only one not to understand this reference? Please pardon my dense-ness, if that's what it is ... but can you help me get what I'm missing? Thanks!

  6. #56
    Junior Member stlmichelle's Avatar
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    Probably the first time I slid a pair of pantyhose up my legs. I had found myself drawn to them at a very young age, but the feeling that a pair of pantyhose give for the very first time is more intoxicating and addictive than any drug.

  7. #57
    Transgender Person Pat's Avatar
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    Quote Originally Posted by Lori Kurtz View Post
    ... but can you help me get what I'm missing? Thanks!
    The meme is that Al Gore invented the Internet.

  8. #58
    Oh to be an English Rose Jane G's Avatar
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    Without doubt the first time I walked out of a department store with a bag full of girlie stuff, just for me. Such a guilty pleasure and never to be forgotten.

  9. #59
    Member Kathy Smith's Avatar
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    Oh, which one?

    Probably my first wig, bought on a market stall (nervously - and wondering if all wig sales are recorded...).
    I'd hung a cheap mirror on the back of a bedroom door and the face that looked back at me was Kathy's. That was amazing.

    My other choice would be my first pair of silicone forms. Not exactly the highest quality, but the difference they made to me was astounding (although I suspect some of that might have been in my imagination. lol
    Last edited by Kathy Smith; 06-13-2016 at 01:24 PM.
    **-* Kath *-**
    Let them see that their words can cut you and you’ll never be free of the mockery. If they want to give you a name, take it, make it your own. Then they can’t hurt you with it anymore.
    ― George R.R. Martin, A Game of Thrones

  10. #60
    Senior Member Lori Kurtz's Avatar
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    Quote Originally Posted by Jennie-cd View Post
    ... Al Gore invented the Internet.
    Ah ... cute ... ... Thank you, Jennie.

  11. #61
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    The first time trying on dresses in a store. I browsed for ages before I finally admitted to the SA that I was looking for items for me. She was wonderful.

    Then, just last week going out to the theatre with a GG fully dressed for the first time. It was such a good night.

  12. #62
    Silver Member ClosetED's Avatar
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    Like others, the first time I looked in the mirror with wig and makeup and saw the woman I only dreamed of magically turning into.
    I also recall the one time, during college, of going out in public, to a movie. I passed as far as I know, but so scary I did not try again.
    Hugs, Ellen

  13. #63
    Silver Member Elizabeth G's Avatar
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    These have been a lot of firsts for me but the feeling I got the very first time I walked out the door fully en femme was probably the most terrifying and simultaneously exhilarating feeling I have ever had in my life.

    Beth

  14. #64
    Senior Member
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    Quote Originally Posted by Jennie-cd View Post
    The meme is that Al Gore invented the Internet.
    If you look close at those brows he may have had ulterior motives

  15. #65
    New Member ChristaB's Avatar
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    I had dabbled in trying to put on make-up a few times, never with success, because I never really knew the basics. So I finally hired a professional make-up person who specialized in crossdressers. During the whole process she explained to me what she was doing and why she was doing it. I could see the transformation as she went through all the steps. When she was finished, she helped me put my wig on, and I was amazed at the look I (or she) had accomplished. Not only did I look like a woman, but I felt like a woman, I felt complete. And yes, there are still a number of firsts for me to undertake ...

  16. #66
    There's that smile! CarlaWestin's Avatar
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    I also remember the first time one of my threads got over 100 replies.



    Oh, wait. That hasn't happened, yet.
    I've waited so long for this time. Makeup is so frustrating. Shaking hands and I look so old. This was a mistake.
    My new maid's outfit is cute. Sure fits tight.
    And then I step into the bedroom and in the mirror, I see a beautiful woman looking back at me.
    Smile, Honey! You look fabulous!

  17. #67
    Member marlacd's Avatar
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    Oh Well! Let me help you along!

    I had several firsts. When I lost the leg fur and put on panty hose for first time.

    When I got my first pair of heels that fit me correctly. (Mail order, I have BIG feet)

    The day I got on the 'net and found out there were dozens of ladies just like me.

    The day my upper lip had seen daylight in 18 years. (And found out I looked years younger without a mustache)
    I don't dress up because I want to be a woman, I dress up to make me happy.

  18. #68
    AKA Lexi sometimes_miss's Avatar
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    Firsts....hmmmm. At 15, the first time I put on a cute minidress outfit that my 19 year old sister wore when going out clubbing, doing my hair like hers, make up as best as I could, looking in a mirror and seeing a very hot teen age girl looking back at me. It pushed me into may more years of wondering what I was supposed to be. It was during the regular school year, I was playng hooky, both parents were working, my sister wouldn't be home until after six that night. I had the whole day to be a hot girl. And loved every minute of it. Even went outside to get the mail, figuring if anyone saw me, they'd mistake me for my sister, as by that time we were almost the same height, and we were both very slim. As I had on one of her bras, who could tell from a distance?

    The first time I ordered my own girl clothes. I was....18? I had gotten a Sterns dept store credit card, and with each bill, came an advertisement for something. One month, it was a cute camisole and tap pants. I spend a while before ordering, but did it. Of course, everything went well, and I had my first official girl underwear of my very own. More clothes were to follow. I was always paranoid that someone I knew might have a job with the shipping dept at Sterns and wonder why I was ordering so many woman's things.

    But the biggest first that I remember the best? Nope. Wasn't sex. And it had nothing to do with crossdressing.

    It was buying my first car, and driving it home. By myself. Dad followed in his car, of course. But I had worked all winter to save enough money for it, and it was the exact one I wanted. And it was exactly as wonderful as I had always dreamed it being. Over the next year, I spent every spare minute behind the wheel. Over 40,000 miles that year, which means nearly all my spare money went to paying for gasoline. But it was worth it.

    Three years later, I re-lived that type of experience when I bought my first motorcycle, and drove that one all over the place, too.
    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.

  19. #69
    Aspiring Member
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    Getting fully outed by my parents almost a year ago. Sure, they weren't too happy about it, but there was a sense of relief I've accepted and am more than grateful for.

    On that note, phoning a counselor trained in LGBT matters. They (singular) were among the more understanding individuals I've poured myself out to. Even though it was sadly a one-off affair, it was a considerable leap forward for me to at least come to terms with this side? part? of me.

    Earlier than that, wearing a minidress for the first time. I was still too young to club, I simply thought the dress was cute (if a tad too revealing at the legs) and fluffy. I still like that dress, but I don't really have many venues for it. As you can imagine, it's a bit hard to go anywhere with a skirt that blatantly exposes the top of my stockings.

  20. #70
    Coulda, woulda, shoulda.. PattiMichaels's Avatar
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    ...first time I gave myself a meticulous pedicure.

    ...first time I shaved my legs, chest, and underarms.

    ...first time I saw myself in the mirror after a professional makeover.

    ...first time I attracted the look of a cute guy even though he knew who I was underneath the veneer.

  21. #71
    Aspiring Member
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    It was the first time that I was fully dressed with complete makeup.

    I looked so much younger and felt great dressed as a woman.

  22. #72
    There's that smile! CarlaWestin's Avatar
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    Now I'm remembering a lot of firsts. This one just came to mind.
    The first time I got clocked. I was walking around an urban area in the restaurant district.
    A couple passed by on the sidewalk and I distinctly heard the woman say,
    "I've heard of that! A man trapped in a woman's body."

    (Insert straight face smiley, here)
    I've waited so long for this time. Makeup is so frustrating. Shaking hands and I look so old. This was a mistake.
    My new maid's outfit is cute. Sure fits tight.
    And then I step into the bedroom and in the mirror, I see a beautiful woman looking back at me.
    Smile, Honey! You look fabulous!

  23. #73
    Senior Member BrendaPDX's Avatar
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    The first time I bought womans underwear and paid for it. I was so nervous I didn't want to wait for my change. The first time I used a changing room, the attendant asked how many articles of clothing I had, she counted them out and didn't say a thing.

  24. #74
    Aspiring Member Desiree2bababe's Avatar
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    First time I pleased a man and the first time a man treated me all evening as a woman, asking for a second date!

  25. #75
    Silver Member ClosetED's Avatar
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    Typical first - first time I put on my mother's pantyhose from the hamper and got sexually aroused for first time.

    Finding real silk stockings in trunk in basement (possibly from a grandmother)

    First time I obtained my own hosiery - sent for free sample of Silkies.

    Hugs, Ellen
    (Closing in on 100 posts Carla!)

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