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Thread: Going on vacation as a Crossdresser

  1. #1
    New Member
    Join Date
    Jul 2020
    Mobile, AL

    Going on vacation as a Crossdresser

    Have you ever wanted to go on vacation or been on vacation as a crossdresser? I plan to go to Florida soon and was thinking of spending some of my time dressed as a woman. I like to hear from those who has done this. Now I have done a weekend or a couple of days during the week out of town dressed up and enjoyed it. Got a few compliments on my outfits. I iwll be careful due to the virus outbreak

  2. #2
    Member VS Fan's Avatar
    Join Date
    Oct 2009
    Would love it ... most vacations at this point in my life have included family and as such, Kelly has had to stay home. But on the other hand, it was a big step for me to take out the trash dressed this morning under cover of darkness haha! I have done plenty of long distance driving dressed however, but always change back in the car before checking into a hotel.
    Kelly a.k.a. VS Fan

  3. #3
    Member Joyce Swindell's Avatar
    Join Date
    Mar 2016
    Orlando, Fl
    Long weekend to the Southern Comfort convention. Left on Thursday morning and wore NO male cloths all weekend! It was awesome. Went to dinners, a live show at Lipps, swimming, shopping, meetings and so much more. I missed the last one and am really looking forward to the next one.

    So in answer to your question... vacation... not really but I do plan on retirement and wearing what I want when I want!😁

  4. #4
    Platinum Member
    Join Date
    Jan 2010
    I’ve made several cross country trips in girl mode - north and south - through America’s midsection. Even in relatively small rural towns in KS and OK, I felt that I was accorded every courtesy, even properly pronounced

    My dream, post covid, is to travel Europe as a transwoman, especially countries like the Netherlands and Scandinavia, where women are taller on average

  5. #5
    Senior Member Jean 103's Avatar
    Join Date
    May 2013
    Central Coast, CA
    Yes I've done it, and the next one is in 24days. Halloween in Vegas.

    Diva Las Vegas/DLV is a week long vacation for CDs. Normally takes place around April, I've been twice. This year it was moved to the end of October ,than it was cancelled a few days ago.

    I'm still going and now I have 7 of my friends coming from my home town. Halloween is on Fremont Street in Vegas this year if anyone wants to join us pm me.

    For you it's a big deal, for everyone else, not so much. So don't worry or over think it. It's all been done before, relax and enjoy your trip.

  6. #6
    Senior Member
    Join Date
    Nov 2004
    Why not?

    You are in another town nobody is going to recognize you or ever see you again.

    Crossdressing on vacation is basically how I got my start going out in public.
    Last edited by Robertacd; 10-02-2020 at 01:48 PM. Reason: more to add

  7. #7
    Member FrannGurl's Avatar
    Join Date
    Sep 2016
    I would LOVE to take an actual vacation dressed the whole time. I've only done weekends though. It was both nerve wracking and wonderful at the same time! Once at the beach with a woman friend of mine, and twice in the mountains with an exboyfriend to restaurants and shops in a small town. The beach was the most nerve wracking though, being out in public around the hotels and the boardwalk with my friend wearing short Summer clothes. I did finally get the nerve to wear my black one piece swimsuit on the beach in the early evening while the sun was still out and there wasn't so many people...Tucked very well, along with a few drinks first to calm me down!

  8. #8
    Exploring NEPA now Cheryl T's Avatar
    Join Date
    Feb 2006
    Yes, the wife and I did an "all girls" vacation about 10 years ago.
    We traveled throughout New England for a week sightseeing. We went to Acadia National Park in Maine, shopping at LL Bean and all the other shops in town. We took a tour of Ben & Jerry's Ice Cream and the also the Vermont Marble Museum. We stayed in all types of hotels and ate at everything from Dunkin for breakfast to a fancy hotel restaurant for dinner with McDonald's in between. It was a fabulous week and I really hated to have to return home and work.
    Wear what makes you feel Confident !

  9. #9
    Gold Member bridget thronton's Avatar
    Join Date
    Jun 2006
    Michigan USA
    I have done vacations where I wore dresses and skirts most of the time

  10. #10
    Weirdest woman ever! docrobbysherry's Avatar
    Join Date
    Sep 2007
    Orange County, Calif.
    I'm a CD and I've done weeks at a time at T conventions and gatherings around the country.

    But, have also taken Sherry with me to other countries. Where she sometimes shows up in the strangest places!

    P1410529 (640x596).jpg
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

    Challenge yourself and pursue your passions! When your life clock runs out, you'll have few or NO REGRETS!

  11. #11
    Platinum Member Teresa's Avatar
    Join Date
    Dec 2013
    If it wasn't for the Covid 19 situation I would have travelled more this year , OK in my case it would be as a TG .

    I would like to do a cruise next year depending on the safety angle .

    Maybe one point is don't go looking for special priveleges because you're a CDer because you maybe disappointed , I hope I can travel as normally as possible , I'm simply going to do it as a female . Please also consider the compliments may be made by people knowing you are a guy in a dress , that's why I'm not too bothered if I don't get compliments because it means I've passed under the radar .
    The real me , no going back.

  12. #12
    Gold Member Helen_Highwater's Avatar
    Join Date
    Jan 2010
    Midlands UK

    Many times; I've always rented a small cottage/house usually somewhere quiet for a week and once through the door and unpacked the drab stuff stays in a holdall. I'm enfemme 24/7, sleep enfemme and from the moment I get out of bed it's wig on and spend the whole day enfemme out and about.

    It can be tiring, showering, shaving makeup, getting dressed for the day and then re-doing the makeup and changing to go out in the evening and then cleaning makeup off at the end of the day, shower before bed. Plus spending time out in shoes that felt fine around the house but when worn for a days shopping leave your feet screaming for mercy.

    Would I change it. Not on your life! Being out and about, shopping, eating, cinema, traveling on public transport, engaging with SA's, members of the public, just being another woman going about her business. Feels so good.

    There's a post of mine regaling about how I was due to spend a week away in November but due to covid I've now moved that to Feb of next year in the hope that the covid situation has improved and there'll be fewer impediments to getting out in public spaces.
    Who dares wears Get in, get out without being noticed

  13. #13
    Aspiring Member
    Join Date
    May 2014
    Pacific Northwest
    Read Susan Miller?s blog. She has done several two-week vacations to Las Vegas, staying dressed from the time she departed Portland to the time she returned. She also just finished a ?stay-cation? in Portland last week.

  14. #14
    Just finding my way.... StaceyJane's Avatar
    Join Date
    Oct 2008
    Harker Heights
    The best I've done is flew from Austin to New Orleans as Stacey. I did pick up my rental car and check into my hotel as her and it was s great.

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

  15. #15
    Silver Member
    Join Date
    Jan 2016
    Orange County, California
    Two memorable one week trips to Las Vegas for Diva Las Vegas. I was fully femme driving there (and back), lunch break, fuel, and nature call stops included. Checked into the Flamingo dressed and stayed en femme 24/7 with a bunch of wonderful ladies. This year? NO ..Covid is too risky at my age and medical facts.

  16. #16
    Gold Member Lana Mae's Avatar
    Join Date
    May 2016
    North Carolina
    Transwoman, so 24/7/ 365!
    I started as a crossdresser! I needed confirmation and booked a transformation and a shopping trip for a wig(I had none at that time!) It was 24/5 vacation and I loved it! When it was all over, I just cried and cried! I did not want it to end! So yes if you are ready, DO IT! Hugs Lana Mae
    Life is worth living!
    "Foxy lady! You look so good!!" Jimi Hendrix

  17. #17
    Silver Member CynthiaD's Avatar
    Join Date
    Jul 2011
    I’ve been on several crossdressing vacations. In fact, I can’t remember the last vacation I had that wasn’t a crossdressing vacation.

  18. #18
    Aspiring Member JocelynJames's Avatar
    Join Date
    Jul 2012
    Gardner , MA
    I have not but mentioned it To my SO as a goal this year pre-COVID. Just a day would be a huge step for me.
    Last edited by JocelynJames; 10-02-2020 at 07:23 PM.
    If you only knew the power of the pink fog! ~Joss

  19. #19
    Gold Member
    Join Date
    Aug 2009
    A trip like you are planing would diffidently be on my Bucket list.
    The best I can do is to go out dressed in my car for an errand or two.
    Where I do not have to get out of the car

  20. #20
    Aspiring Member TheHiddenMe's Avatar
    Join Date
    May 2016
    Metro East area near St. Louis, Missouri
    I'm retired so it's not a vacation but I have traveled out of town to dress to San Francisco, Cleveland, and Chicago twice.

    My first trip to Chicago was on the train and I wrote about it in this thread.

    It sounds like you have done it before so why wouldn't you do it again?

  21. #21
    Senior Member Princess29's Avatar
    Join Date
    Sep 2005
    Queensland, Australia.
    Like others, I had my travel plans screwed by Covid this year but I had planned on going to Las Vegas in March for the Diva Las Vegas event and was going to try and spend a lot of time dressed up and was looking forward to playing golf dressed again and a few other events. I have done a few trips to Sydney to attend a TG event but as I work at a domestic airport in queensland, I couldn't fly dressed up anyway as I wouldn't be able to pass through a screening point without running into someone that I know.

  22. #22
    Connie Connie D50's Avatar
    Join Date
    May 2006
    Southeast WI.
    I have had great weekends away with my wife dressed the whole time.

  23. #23
    Silver Member Sometimes Steffi's Avatar
    Join Date
    Sep 2008
    Nation's Capital
    I've talked about it before, but I've gone to the Keystone (CD/TG) Conference 9 years in a row until they cancelled Keystone 3030 due to Covid. At first I travelled in boy mode and transformed when I got there and was Steffi 24/4. A couple of times I went with a CD friend and transformed at her place and was en femme 24/5, including travelling by car and check in/out. One of those times she dared me to leave Plan B (my boy clothes) at her place, which I did.

    While at Keystone, I went to the casino, to a restaurant and clothes shopping, mostly with large groups of CDs. I've gone to an urgent car center to get stitches removed, my battery died and I had to call AAA for a jump service, and I'm still here to talk about it.

    My wife is totally not into it, so I could never go on a rea vacation with her en femme. But, I would if I could.

    Go for it.
    Hi, I'm Steffi and I'm a crossdresser... And I accept and celebrate both sides of me. Or, maybe I'm gender fluid.

    Gender fluid (adj.) - Describes a person whose gender identity is not fixed. A person who is gender fluid may always feel like a mix of the two traditional genders, but may feel [more] like one gender some days, and [more like] another gender other days.


  24. #24
    Member StephanieM's Avatar
    Join Date
    Dec 2016
    I live in Tallahassee. If you are near here shout out, I know some places to hang out where no one cares what you wear.

  25. #25
    Amanda countrygirl's Avatar
    Join Date
    Oct 2007
    Sandston, Virginia
    I have always wanted to be Amanda on vacation and stay as her the whole time.

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