Need advice-- how to prepare for big vacation

[Aka_Donna]

Wow, we have finally reached a point where we are ready to try being out, not locally, with me dressed. Both of us are nervous about it. We plan to spend a couple days away. What have you learned about the first times out that helps wife increase comfort level with dressed partner.

Thank you.

[Helen_Highwater]

Time spent away from home enfemme, I'm your girl.

You didn't say what type of accommodation you're staying in but let's opt for hotel. Your first big hurdle is leaving your room and making your way through the lobby. Your only real option is go for it. Deep breath, head up and be as casual as you can be. My guess is both of you will have butterflies but once outside they will start to subside. Oh, Don't overdressed. I guess you might want to go for some retail therapy so sensible shoes will be your friend. Walking in heels for those new to being out and about can soon get very uncomfortable.

Go for a drive. Give yourselves time to acclimatise. Then consider a drive through fast food. It's a quick interaction with someone, someone who's likely not to be paying too much attention. Park up, eat your food and then get out the car to put the litter in the bin. It's a quick intro into being in a public place.

Crowds are your friend. As I've said before. If you're in a hall with 10 others, you'll notice all ten. In a hall of a hundred, you'll still only notice ten. And this is where dressing conservatively pays off. Blend in to the crowd. You'll be surprised just how little attention others pay to their surroundings.

If you do go shopping, actually look for an item. A skirt or dress. Jewelry, shoes. One it stops you looking like shoplifters and two it helps you focus away from thinking everyone is looking at you. Try not to look to see if anyone is looking. Just go about your business.

Once you've been out for even a short while your confidence will grow, nerves will calm, enjoyment will take over. It does help to have a plan mapped out. Places you might want to visit check them out on Google Street View. Helps you feel more confident if you know what a place looks like, parking etc and stops you ending up somewhere that might be " a little rough".

Have a list of things you'd like to do. Visit an art gallery or museum, cinema, zoo. Having predetermined options stops you just floundering about. Being at a loose end. You don't have to do all of them but it gives you options.

There's no magic wand that'll get you over the first few minutes. But be assured, some many here have gone before you and come out not just unscathed but eager for more and that says more than any advice you'll get.

[Philippa Jane]

Excellent reply Helen.

[audreyinalbany]

dress to blend. Generally I'd recommend picking a mainstream venue. I'm a big fan of museums so I'd opt for that. Generally folks at museums haven't been drinking and they're not looking to antagonize anyone they're jsut there to learn and enjoy the exhibits. Movies are also a great option. You get a chance to interact on a limited basis with ticket sellers and others in line and then you get the break of sitting in the dark for a couple hours where you can kind of forget that you're crossdressed. Afterward go where 'the movie crowd' goes: nearby restaurant or bar, oething quiet and low key.

[Aka_Donna]

To help focus replies.. it will either be a pet friendly hotel on coast or a vrbo rental. Ocean views are critical. Outfits are knee length skirts/dresses with non-bold colors and almost no makeup, slight foundation, blending lipstick, touch of eye treatment, wig and boat shoes. Maybe black hose to mute legs. So definitely a blended look. It's more concern about what uncomfortable situations we might encounter. It's california so restrooms should not be a problem. Although there are Karens everywhere. Were mature and somewhat handicaped, so no one would think of picking us up. Mostly looking to walk by ocean/beach and eating a meal out dressed. Sounds simple, right? Just first time, so jittery...

[Cheryl T]

Well, for us it was to act as girlfriends.
You will probably still have the tendency to hold the door for her and things like that. Don't! Girlfriends don't do that.

Don't spend your time looking at others to see who's looking at you. Just do what is natural for wherever you are. On the beach then enjoy the beach and the surf, in a mall, then look at all the pretty clothes, not the shoppers.
Relax, be just another person doing whatever you are doing and forget the world around you.

[docrobbysherry]

Donna worry, Donna! U have a Golden Ticket! As long as u r out with a female you'll find u have a pass to go nearly anywhere!

T's out by themselves may be considered pervy by some. But, being out with a woman provides validation to everyone that you're NOT up to no good!

[TheHiddenMe]

Here's the reality; you are EXTREMELY unlikely to encounter any uncomfortable situations.

Plus, I assume by the coast and your current location you mean California, which is one of the most progressive states in the country if not the world. I've been out dressed (briefly) in LA and San Francisco, and didn't have an issue. My wife and I have spent about four weeks in California the last two plus months, from north of San Francisco to Coronado near San Diego. There are tons of people of all types of dress, nationalities, accents, etc. You'll just be another two of the thousands you will see.

The thing you will mostly find is there are no torches and pitchforks. Most people are doing their own thing OR looking at their phones.

Here's my advice. Just quit worrying and do it. You don't need to do anything special. Get dressed, open the door, walk outside, get in the car, drive somewhere, walk along the beach, go to a mall, go to a coffee shop or cafe, or whatever you want to do. And if people have an issue, that's THEIR problem, not yours.

[Fiona_44]

Wear sunglasses as much a possible. The eyes give away a person's nervousness. Other than that, just relax and enjoy. You may think everyone is staring at you but in reality they're not.

[Kate Jennings]

Well done, Helen!

[Helen_Highwater]

I'm going to suggest something that for me at least was one of the best things I've done to improve my dressing.

Go get your foundation checked at a beauty counter. Foundation, as the name implies, is what you build your look upon. For years I'd worn what I thought would serve me best. Turned out not to be the case. Way too pale, more circus clown than floorless femme fatale.

St in the chair no-one will pay you any attention. The SA will treat you like any other client. You'll be advised about what blusher, lippy, highlighter will suit you best. Might cost you a few dollars in product but it's worth every cent. Getting and knowing the basics are right gives a major boost to your confidence.

Another thing I'd suggest is visiting a wig salon. Check out their prices online first. Some can be prohibitively expensive. Being able to try on different styles can be an eye opener. I never though short cuts would suit me but having tried a few on I was pleasantly surprised. I took my wingman Debs to a salon I'd used a couple of times previously. Her old wig didn't look bad on her but the new one she came away with, see her avatar, was soon much nicer and suits her to a tee.

Both the above a also wonderful experiences in their own right. You might say rights of passage. Would highly recommend.

[abby054]

I agree, Helen. I first got my foundation checked fifteen years ago in Boise, Idaho. Boise was not, at that time, a place with a progressive reputation. It still is not, though Boise has mellowed considerably. I went in drab to a dept store cosmetics counter. Yes, in drab. The SA sat me up in the chair and went to work. I reaped a little attention from a few mall goers but none made any trouble. We left the foundation in place when I departed. She gave me a tiny sample bottle of what we decided on. I bought a full regular size bottle. The SA did some productive work for me so it is only fair that I pay commission. The product served me well.

I also have been to two wig salons in the past five years, one in Portland, downtown but east of the Willamette River, and the other in Phoenix, actually Old Town Scottsdale. Again, in drab both places. In Portland, the SA fitted me for a wig in a chair in the open salon with everyone else. We found a wig that I liked but I felt rushed. The salon mailed it to my home PO Box. The SA, also male, exhibited no enthusiasm. I was treated professionally but I just did not get good vibes. In Scottsdale, the SA offered a semi private room. Not the big bull pen out front but there were maybe three customers in that room. The SA treated me like I owned the place. We soon found a wig that I liked. It was a shorter style than I favored previously. It was brown with enough gray to match my hair in drab. The salon mailed it to my home PO Box and included ample supplies to maintain and style it. It quickly became my favorite wig. The Portland wig never really felt right, though it was long with curls, the same color as my hair in my youth, a truly beautiful wig. Neither experience was frightening or even mildly unsettling, but the experience may have influenced my thinking.

Both the makeup experience and the wig experience were in drab. They went well. I have no fear of repeating them.