Going on vacation as a Crossdresser

[CDJamie2000]

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

[VS Fan]

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.

[Joyce Swindell]

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!😁

[kimdl93]

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

[Jean 103]

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.

[Robertacd]

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.

[FrannGurl]

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! :heehee:

[Cheryl T]

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.

[bridget thronton]

I have done vacations where I wore dresses and skirts most of the time

[docrobbysherry]

I'm a CD and I've done weeks at a time at T conventions and gatherings around the country.:hugs:

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

316108

[Teresa]

Jamie,
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 .

[Helen_Highwater]

Jamie,

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.

[abby054]

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. http://susanmiller64.wordpress.com/

[StaceyJane]

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.

[Jenny22]

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.

[Lana Mae]

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

[CynthiaD]

I’ve been on several crossdressing vacations. In fact, I can’t remember the last vacation I had that wasn’t a crossdressing vacation.

[JocelynJames]

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.

[RADER]

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

[TheHiddenMe]

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.

https://www.crossdressers.com/forums/showthread.php?248781-quot-Training-quot-Pretty&highlight=

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

[Princess29]

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.

[Connie D50]

I have had great weekends away with my wife dressed the whole time.

[Sometimes Steffi]

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.

[StephanieM]

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.

[countrygirl]

I have always wanted to be Amanda on vacation and stay as her the whole time.

[KellyTerry1819]

I was hoping for a vacation trip this year where Kelly would come out at least part of the time but covid have prevented that from happening. Might be as well since that gives me more time to build up the nerve to go out in public.
/kt

[Christina89]

Every 6 months I take a trip from Massachusetts to Michigan. And I was hoping that before my trip in November they would have opened the US/Canada border. But it doesn't look like that will happen. Anyways I was planning on driving out there with all women's clothing on instead of my male clothing. But sadly it doesn't look like that will be happened.

[Stephanie47]

The best I have been able to do is a "Staycation" for seven to ten days when my wife was out of town/state. I was able to hang up a good number of dresses and slips on hangers and freely load up my armoire with undies and heels lined up at the foot of the bed. I did got out for evening strolls in a safe residential neighborhood. If my height was chopped down to five foot six I'd do the entire experience of shopping. At six foot with no heels and 200 pounds that is out of my comfort zones.

[RachelB.]

Just before covid shut down everything my wife and I spent a fun week in New Orleans. I left home as Rachel and returned as Rachel. We did a lot of fun things including an airboat ride in the swamps. Really had to hold onto my wig that day. Restaurants, bars, and anything we wanted to do. No issues or problems at all.

[NjJamie]

Stephanie, I felt the same way but one suggestion is to go "grey". I have options from blonde to brown but on a lark got a grey wig and have wandered into many stores with no looks at all. I hate to think I'm over the hill but "going grey" has really been fun. Add the mask and some glasses and no one looks twice. I've been to other stores as a blonde and brunette, each time catching someone taking a second look, maybe give it a try.

I'm 5'11", 250 or so and built like a lineman, never thought I could pass at all and I don't think I do, just that no one looks twice at an older woman.

[Aunt Kelly]

Quite so, NjJaimie. For better or worse, "women of a certain age" start to fade into the background, even those of us who have "longer bones" than most. :)
I'm used to it now, and rather enjoy the courtesies which are (usually) offered to those of us who've attained senior status.

CDJaimie2000, as a CD, the big advantage of the destination vacation is that there's nobody there to recognize you, so you can relax and enjoy the experience on a level that might have been tougher at home. Enjoy your trip and by all means, stay safe.

[Vickie_CDTV]

Is it even possible to "go on vacation" right now with this covid insanity going on?

[Jean 103]

Yes, I leave Monday. Besides what is the difference. I have not stopped working, I'm out and about every day.

I'll tell you the difference , I'll be keeping my distance in Vegas with a few of my friends.

I'm sorry but with the rules that is all I can say.

Yes I'll put up pictures.

[fun4metoo2004]

I want to go to Las Vegas after I sell my house. I will have a little money then and want to hit the photo salons and do a full glamour makeup with different outfits and wigs.