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Thread: What's your favorite memory of dressing up?

  1. #1
    Yes, this is really me! shayleetv's Avatar
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    What's your favorite memory of dressing up?

    I have 3 memories about dressing. But this one I think is my favorite. It was long time ago when I was a soph in high school back in 1957. My sister was in college and was a dance major. She had solo dance that she had to perform for her grade in the class she was taking. She would be graded on her interpretation of of the music and words. In the song the girl was auburn and long haired, my sister was short blond. Solution rent a wig from the school's theatrical department. She had the wig home and out of the box and she noticed the way I was looking longing at it. She asked if I wanted to try it on. Eagerly I said YES! She said "Come home right after school tomorrow and I will be ready to let you wear the wig." She used to dress me up as her sister years ago and she knew I still dressed on my own but I guess I was too stupid to put 2 & 2 together to think what she had in mind. When I got home there was a note for me to take a shower and put on the things she had laid out for me on her bed, a bra panties a half slip and a full slip garter belt and nylons. I was so excited I could hardly contain myself. She finally showed up with her friend who taught makeup for the schools theater department. She made my face up and my sister got her hot floral dress for me to wear. It was the in kind of dress that the popular girls wore especially the hot ones, scoop neck and thin arm straps. After they put the wig on and showed me what I looked like I fell in love with the girl in the mirror, she was down right gorgeous. All dressed up and no where to go. When Beth(my sister's friend) saw me completely dressed she said we have to her off, and they did. We went to dinner at a pizza place that I had never been to so we wouldn't run into people that I knew. But we did run into a lot of my sisters friend from school and I was introduced as a cousin from back east. What a blast!!!!!
    "If you could kick the person in the pants responsible for most of your troubles, you wouldn't sit for a month."
    ~Theodore Roosevelt

  2. #2
    The best of both worlds Kathi Lake's Avatar
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    My favorite moment in dressing is usually the last one I had. I'm not sure if that's because I'm a guy and naturally forgetful, or I just take life as it comes to me.

    Kathi

  3. #3
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    My favourite dressing up moment was about a year ago. My wife was out for the evening so I put on some of my favourite clothes which involve an open corset, black stockings, black heels and a little black dress. I also had the wig you see in the photo and full make-up. She knows I dress and sometimes is ok about it, sometimes not. Anyway, she came back early and so I called downstairs to say I was dressed and she said that's fine. What I didn't realise was that she had brought a guy from work back for a drink. I spent the rest of the evening watching him trying to look up my dress. It's not much but I enjoyed it! That's when I realised I could pass.
    Lucy

  4. #4
    Just a little mouse. Babette's Avatar
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    My favorite was the first time that I fully dressed. That's right, hair, makeup, forms, awesome outfit, and shoes. It was like, OMG who is that person I saw in the mirror. Since then, dressing has been wonderful but never as memorable.

    Babette
    Someone else's imagination is a terrible thing to waste.

  5. #5
    Just Being Me Paula G's Avatar
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    My favorite memory is when I was on vacation by myself in a cabin on a lake. It was the end of the season, so no one was around, and I was able to dress all the time. It is also the only time I've been outside while dressed, and have plenty of photos to help me remember.

  6. #6
    Silver Member Jonianne's Avatar
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    My wife taking me on my first outing in 2000 and last year on vacation with my wife at Niagara Falls. Later we took the Amtrak from Plattsburg to Albany which was the first time I went dressed on public transportation. I never imagined in my life that I would be able to do something like that! In my album are some pics.
    Joni

    "Yes, to dance beneath the diamond sky with one hand waving free" Bob Dylan

  7. #7
    Member IwishIwasTracy's Avatar
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    I would have to say trying on wedding dresses at a David's Bridal in Seattle. I loved wearing those gowns.


    Tracy

  8. #8
    Senior Member Sally2005's Avatar
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    A couple decades ago when my wife loaned me her spandex little black dress and we went out to a bar on halloween, this old drunk guy practically fell off his chair at the bar to come to say hello to us at the front door. The door staff kicked him out. But I still remember feeling like a side of beef for a minute. In the bar which we thought was remote enough, we ran in to a good friend who recognized my wife (not me) until he did some simple math.

  9. #9
    happy to be her Sarah Doepner's Avatar
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    I was stressed because I didn't know how my wife was going to react to my dressing after she found out. One day the topic came up and she said to go ahead and dress if I wanted to, but for the time being I needed to stay in the bedroom. She even gave me a project to work on to help her with her work. I dressed in something kind of casual, but conservative and tried to do a very good job on my makeup, just in case. After about an hour she knocked on the door and came in to see how the project was coming along and to finally meet Sarah. We got along well and have ever since.
    Sarah
    Being transgender isn't a lifestyle choice. How you deal with it is.

  10. #10
    Senior Member Christina Horton's Avatar
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    I love all the times that I have been out but I have two witch I think of as one big HOLY SH%T 2 weeks of fun Shocks and laughs .
    http://www.crossdressers.com/forums/...d.php?t=113089
    and this one.
    http://www.crossdressers.com/forums/...d.php?t=112976
    The two happened starting last month form the 26 of July two the 4th of Aug . It would be to hard to right all about them again. But what a whorl wind two weeks. I still am in a high from it. I have lots of good memories of "time in dress" and will have more I am home for the week and when my car is out of the shop I will have more fun fun till daddy takes my ahhhhh "Corvette" away. Now If I could fine someone to go to the night clubs with around here I would have even more fun.
    [SIGPIC][/SIGPIC].....................100% Authentic Canadian Cross-dressing Truckdriver!!!!!!!!!

    (((((((((((((((((((("I LOVE BEING A CROSSDRESSER")))))))))))))))))))

    Link to My 20th high school reunion http://www.crossdressers.com/forums/...d.php?t=112976

    If you don't like my (honesty) well TFB.

    Men are just a single celled orgasm , In a petri dish held by a woman. (Gene Simmons)

  11. #11
    Aspiring Member
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    My favorite time was the only time I had ever been out of the house fully dressed.
    It was some years ago on halloween and I was dressed as a woman (duh).
    It all felt so wonderful, especially when we arrived at the party. After the shock had worn off from those who knew me, and after a few drinks, two of the girls tried to lift up my skirt to see what I was wearing underneath. The great part is that I didn't know those two girls until that night. I loved the wrestling match.
    I never wanted the night to end. There was just something so special, sitting there with my legs crossed, wearing my heels and hosiery and everything in front of everyone, half of them strangers. It felt so free to be like that.
    I'd love to do it again.

  12. #12
    Member Chrissie P's Avatar
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    A man held the door for me as I walked in my hotel.
    " Don't get in the way of my mood swing !"

  13. #13
    New Member Lady Joan's Avatar
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    My favorit time that my SO dressed for me, was the day she came home with clothing she was not use to buying. I asked her to vamp it up, buy a few items that were more sensual and sexy.

    She and a CD girlfriend went out and shopped together, she came back to my place and did a show and tell. How awesome it was to see her and how great she looked.

    Since this, we have been shopping together and I have been directing her to more causual wear, so that we can just do every day things in, as evening wear is great, but not for walking the dog around the block.

    Her wardrobe is expanding. Laughs... but I think she loves it, as I can see the beaming smile upon her lips.

  14. #14
    Member suspender's Avatar
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    i tend to agree with the last is the most memorable, even though i remember the first as a kid. most of the time i try to outdo the last thing i did 'coz its so addictive!

  15. #15
    Senior Member
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    I have had many moments that stand out in my mind, but the one that is most memorable has to be the time my wife was away for a week and I was able to be Nicole 24/7 for a week. During that time, I was able to do many new things that I had never done before.

    That week allowed me to drive over 500 miles round trip, go out of state and drive across 4 states, stay overnight in a hotel, eat all of my meals in restaurants for 2 days and of course use a ladies room.

    I will be experiencing another week of Nicole 24/7 in early October and I am thinking of new 'firsts' for that week...

    Nicole

  16. #16
    Member carrie-ann's Avatar
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    I have a lot of memories but yesterday for me was so great I wore a long black skirt with a purpurl blouse to work. It felt so nice and sexy to me and naturel. Every one thought I looked nice. Had good comments. And a lot of support for me being me. Like they said as long as I'm happy I am very happy. And not to forget the hosery and panteis and and make-up.

  17. #17
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    Well, I have been dressing for many yrs. And although I am able to dress with my girlfreind, I must say that my favorite memory to date was last yr. when i first was able to dress freely with my mother.
    My first experience dressing in front of her was so wonderful. She was completly accepting. Just the simple things, like getting up in the morning, being able to make the coffee, in just my lovely foundation wear, with stockings, pumps, full slip, was so exciting for me.
    On that first evening, I asked her if I could handwash some things in the guest bathroom. She said of course. So there i was, in my things, washing out some stockings, panties, one of my corselettes in the sink. It just felt so natural. I left the door open, and she could see me from the den. I hung my things on the shower curtain rod to dry, and everything looked so nice hanging there.
    I love ff seamed stockings, and she remarked on how "old fashioned" they were. I simply stated that i really loved the look. Ane she did comment on how nice they looked on me. She also found it rather amusing that I could go all day and night in a girdle or corselette. I just told her that i loved the look and feel so much, and that these items, (along with sheer gartered stockings) were essential for me in order to feel "content" and complete when i dress. She understood how I felt after I explained it.
    I think that one main reason I enjoyed being with her like this, is because the sexuall aspect of my dressing was secondary at that time. It was more a feeling of freedom to be myself with her, and how comfortable she made me feel. Of course there were times during the day when I would go into my room and close the door for breif periods, and she would respect my need to be alone. (pretty sure she knew why...lol)...
    So, that is my favorite memory to this date, but My next visit with her is approaching soon, and I think it will also be most memorable, as I will take it just a bit further this time, in that I will be compltetly feminized, with wig, makeup, nails, etc. I can't wait...............

  18. #18
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    either the firsttime i was dressed at age 7,i was forced back then by my parents who dressed me in my sisters school uniform with a blonde pigtales wig for a fancy dress day
    or the first time i got dressed up in my gothic lolitta style maid dress which was last week.

    stacy marie

  19. #19
    Complex Lolita...
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    Quote Originally Posted by shayleetv
    What's your favorite memory of dressing up?

    [SIZE="2"]For me it was simply driving to Maine all dressed up a few years ago. I was dropping off some of my artworks at a gallery there, and it was a beautiful late spring day, so I dressed extensively for the occasion. Usually my senses would be on high alert when I was out in public like this, but this trip was so relaxing I had no feeling of vulnerability at all. It seemed very natural to be dressed as a woman, and I would stop periodically to walk around, have some coffee, or touch up my lipstick. I drove back to my home in Massachusetts later that day, without incident, through the Boston traffic. I never wanted to leave my cocoon of femininity, but, alas, I had to…[/SIZE]

  20. #20
    Aspiring Member Jaclyn NM's Avatar
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    The best, was the first time I got all dressed, and madeup, and went out in public. What a thrill it was. I'll never foget how wonderful it was.

  21. #21
    Aspiring Member
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    Mine was when I first got dressed completely - in lace bra,panties, slip and hose(all black) and a green velvet dress, high heels,makeup, and for the first time a real wig,not a Halloween costume wig. Although I had been wearing all the clothes and dabbling in makeup since my early 20's, this was the first time I had worn a real wig, and when I finished gettting dressed, looked in the mirror, I couldn't believe it!! With the exception of my hands I think I would've passed, although I wouldn't nowadays. Wish I could get back to those days!!

  22. #22
    Lingerie Lover RachelDenise's Avatar
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    My favorite moment was my first bra fitting. It happened in a small bra salon, and I was wearing only panties at the time. Magical to say the least.
    Rachel Denise

    [SIZE="2"]“One day Alice came to a fork in the road and saw a Cheshire cat in a tree. ‘Which road do I take?’ she asked. His response was a question: “Where do you want to go?’ ‘I don’t know,’ answered Alice. ‘Then,’ said the cat, ‘it doesn’t matter.' "
    - Lewis Carroll
    [/SIZE]

  23. #23
    Just finding my way.... StaceyJane's Avatar
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    My favorite memorie is last summer when I got to try on somes wigs at a profession wig salon. The people there are very TG friendly and they let me try on so many different wigs with so many diffrent looks. The best part was when I found some wigs that looked good and I dressed as Stacey and walked around the store wearing them. I was able to look at myself through the mirrors and it was like I was seeing myself for the very first time.
    Stacey

    I'm not a doctor, I just play one on TV.

    http://www.youtube.com/watch?v=Wob7zmvVTb8

  24. #24
    Carole carhill2mn's Avatar
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    I would not be able to pick a "favorite". I can think of a great many that would qualify.
    Hugs, Carole

  25. #25
    Silver Member
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    I had never been "out" before and had only been CDing for a short period of time. I went for a transformation (make up/wig) for the first time in Las Vegas and thought I had my female clothes to change into in my car. I then found I had forgoten my dress/heels bag in my room. I had to walk from the parking lot, into the casino, past security, into a crowded elevator and back to my room in guy clothes. I was was a stunning female from the neck up but cool guy from my shoulders down. The only thing I could do was to act like this was how I dressed all the time. It worked! Not one stare. I actually enjoyed the unplanned experience.

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