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Thread: My first 'Dressing' experience!

  1. #1

    Default My first 'Dressing' experience!

    Hi all,

    Had my first crossdressing experience on Monday (unless you count hoop earrings, many men wear the gender neutral kind you find at Target).

    I was at the mall and was looking for a bodysuit or one-piece swimsuit. had always been curious. Anyway I found some leotards at Forever 21 that I passed on because they looked far too small for "my friend" for whom I was buying a gift. (wink wink) Then, found a sale on Dolfin one-piece swimsuits at Scheels. So I bought one, guesstimating my size. Well, upon taking it to another store's dressing room and trying it on (with underwear, of course, I'm not a barbarian) it was too small, even the next size up, a 40, which was their largest size, was not tall enough as I'm around six feet. So I returned it.

    I ended up buying a 'skater skirt' in dark silver from Pacsun. I put it on and absolutely loved it from the first second, and not only from the crossdressing point of view. It's just plain comfortable! Why didn't the whole 'kilt' resurgence take off? Guys just don't know what they're missing.

    Of course it doesn't feel quite 'complete' in Hanes briefs, from a crossdressing point of view. I'll have to pick up some more essentials. Any Ideas? I managed to smuggle the skirt home under my mom's nose (she drove us) with the simple expedient of bringing a day pack. I'm becoming quite the 'personal items' smuggler.

    Anyway, this is my intro to the crossdressing side of the site. What would I call myself? I don't feel childish, maybe 17-25-ish. I don't like the sound of the term "sissy". Always reminds me of bondage and dom/sub, which isn't really my cup of tea. Somewhat tomboyish, hence why the name 'skater skirt' jumped out at me. I like the name Ester, too. Classy yet unusual.

    Anyway. Cheers.

  2. #2


    Congrats! I am brave enough myself to make the occasional counter purchase, but only that brave so far. The other day though I managed to walk the dog wearing a pair of 'water shoes' that I could have easily passed off as being more comfortable in the heat (they are). A 'kilt' would be something to dream for, had I not lived where those around me judge for lesser issues. The majority of my own wardrobe is more adult as well and I don't take offense to using the term 'sissy' for lack of a better description - my regressive alter ego isn't as yet fully developed, so if it ever came to being in an actual relationship I'd more than likely pretend to put up a fight

  3. #3


    sounds like someone is almost ready to start saving for their SRS and breast-augmentation surgeries.... (devious grin)

    seriously though, i wish you very good luck with your foray into the exciting new world of cross-dressing and passably transvestism. there are so amny fun things ahead of you....

  4. #4


    If you choose to wear a "Kilt" it is a whole nother experience.
    The garment is so male that no one will comment derogatory about what you are wearing - more like off (kilter) jokes about what is worn or not as underwear !
    I wear kilts that are much shorter than the standard knee length (24 inches - belly button to knee) look at a website - and check the women's kilts.
    I have two of the ultra mini-kilt tartans in 12 inches and wear them over leggings for winter wear.
    For other activities I have 4 of the mini-kilts in 16 inches and with a black brief underwear it is all that is required to prevent an exposure.
    These are fine for sporting activities tennis etc. but with caution at golf courses !
    I also have formal length tartan kilts with the kilt sox; flashes; tux shirt; bow tie; Prince Charlie jacket and sporran when I want to knock'em dead !

    But getting away from pleated tartan wear to wear an "A" frame skirt (just like your skater skirt) and silky blouse or polo shirt with reverse button placket;
    short ankle sox and loafers or Mary Janes is really going to make a buzz !
    At first stay away from my favorite color "PINK" and pastels - you will be pushing the buzz a bit too much too fast. Stay with darker colors black; navy blue
    or dark grey. Going with reds or vibrant colors is an invitation to be too loud and pushing the clothing envelope. Your dark silver is a good starting point.
    Beware if you are a hairy beast - too much body hair and something is lost in making a presentable appearance - it just detracts.

    The only thing to fear is wearing your outfit too early in front of family; relatives and friends and your employer.
    Going the kilt route is the easiest transition over the bridge to clothing freedom.
    Later with age and maturity you will be able to pull it off a lot easier.
    Check out the website for interesting topics and discussion about men wearing skirts etc.

    Making the first leap of faith is always the event that will be remembered by everyone and not everyone will
    accept your motivation and you can't win them all. Break the ice and try your best !
    Last edited by babylock1; 17-Apr-2014 at 03:45. Reason: WEBSITE CORRECTION

  5. #5


    Quote Originally Posted by babylock1 View Post
    Check out the website for interesting topics and discussion about men wearing skirts etc.
    I believe the web site is

  6. #6


    Thank You Baby Denise !

    Went back and edited the post to the correct address of the website !
    For anyone with interests in "UNBIFURCATED" clothing that is the site to visit.

    Bifurcated clothing = pants shorts capris leggings jeggings anything that TWO LEGS go thru.
    UNBifurcated clothing = Skirts Dresses and the alike - no separate leg compartments !

    Once you realize the comfort of a skirt or a dress it is hard to fathom why anyone would
    want any other form of clothing. So why are women wearing mostly pants these days ?
    AND WHY AREN'T MEN WEARING SKIRTS/DRESSES more often ? And it isn't because of fashion !

  7. #7


    [QUOTE=littlelodgewrecker;1176252]sounds like someone is almost ready to start saving for their SRS and breast-augmentation surgeries.... (devious grin)

    Naah, I like the option of switching back and forth. Might get some breastforms, though.

    I'm sooo happy that I got into this. A whole new world is opening up for me and he last few days have been some of the happiest in a while. Loving it!

    Last edited by FootieCrinkle; 22-Apr-2014 at 03:26.

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