Yikes, going into the deep end

[Aka_Donna]

I thought I should start a separate thread on this issue. We have just started talking about taking a 3-5 day trip in the next 6 months where entire time is en fem. This is both exciting and extremely scary at the same time. There are just so many things to consider and learn that I'm worried I'll stumble and I/we will be embarrassed.

Any ideas on how to cope would be appreciated.

Background: Dress three to five nights a week for two to three hours, but it's miad. No makeup and no wig.

Items I need to check out asap and then get comfortable with

-- dressing all day instead of a few hours
-- wearing a wig, after I find one we like
-- walking in heels/wedges for all day without wearing tennies
-- using ladies restroom (big first)
-- changing out earrings, from studs
-- learning eye makeup for droopy eyelids
-- adding time for makeup

My list of items to check off:
-- get fem reading &/or sunglasses. Easy to do, just have to do.
-- get wig and learn how to wear all day. A challenge since I don't even like wearing baseball hats for long.
-- pick out three best footwear and then narrow to two. One for daily and one for evening. Evening heels/wedges are easy, the problem is how to know ahead of time if 2" fat heels or wedges would be better for all day.
-- Learn how to apply eyeliner, eyeshadow and mascara in a way that looks both nice and not totally the same as no makeup. Currently, if I just add mascara, I don't see any real difference after I put the glasses on.
-- do I need a unisex/fem coat/throw as it will be in the upper 40's at night.
-- is there anything that will work for tops with leggings and a mini skirt, or is that too much.

Do not need to be at all concerned with: nail polish, lipstick, finding skirts/tops/dresses/shoes or walking in heels/wedges.


And the big one: how do I make sure all this prep and time and focus does not upset the applecart with wife.

Yes, I know this is a long, long post, but hopefully at least someone here has faced a situation similar and can share lessons learned.

[Laura912]

You are set for an adventure and obviously excited. Who wouldn’t be? Some of the things you are asking can be asked of your wife. A suggestion that the tights and mini skirt should be left at home. Wedges in the two to three inch range more comfortable for long walking as would be a pair of flats. Personally, a nice coat to stay warm would be a definite. Go to one of the MAC or Sephora stores for eye makeup lessons. Have fun.

[Stephanie47]

I saw in your bio that you are retired. First, I'd recommend that you act your age. Mini skirt for me would be out. Knee length dresses would be in. I do not own any female pants; dresses only. Yes, find some comfortable wedges. For evening walks I wear a wedge with a 2+ inch rise. If you have not issues with beard shine I'd go minimal with the makeup, especially if you wear glasses. I have a pair of transition eyeglasses that change from indoor clear to outdoor sun depending on the sun's brightness. I do not see any issues with being en femme 24/7 for any length of time; it's only clothes. When my wife traveled out of state (DADT, here) I had no problem wearing dresses, heels and hosiery and a wig for days on end. I limited my strolls to the evenings when it was dark as being six foot and 200 pounds makes me stand out and thus outside my comfort zone. At his stage of life I'd rather be an oldster at five foot five and 120 pounds. But, that's not to be until the next time around.

[GraceM]

Excited for you Donna. Enjoy. Keep us posted.

[CynthiaD]

I've done the vacation thing, and here's my advice, for what it's worth.

Don't take any male clothing. This includes stealth items like female jeans. This will keep you from chickening out.

Spend as little time as possible in your hotel room. Get out where there are lots of people.

Interact with other people as much as possible. Talk with everybody. Be one of those yack-yack-yack people who never shuts up.

Walk into the ladies room like you own it.

Walk proud like you're a movie star craving attention.

If you get clocked, don't cringe. Stand up straight, stick your chest out, and give them a superior look.

Watch out for obnoxious men.

Wear ballet flats for walking.

[docrobbysherry]

My suggestion if you're traveling with your wife? Take a photo of your post here. Then, delete the post!:eek:

U should have her help u assemble all the items you'll need. And, have her apply your make up, etc. If you're traveling together? This trip won't be all about Donna!:battingeyelashes:

[Helen_Highwater]

Donna,

In 2 weeks I'll be off my annual weekly trip being enfemme 24/7 so this is something I feel qualified to talk about.

As early as possible in your trip go get your makeup done enfemme in store. They'll treat you just like any other customer and you'll get to know what best suits your complexion. Also a great confidence builder.

Footwear: going from a few hours to all day is a huge step so for general day wear flat knee high boots will serve you well. Any heel, no matter how small will take a toll on both feet and legs. Start by wearing low heels for an hour or so and build on that.

Wig: shop in a salon and try them on. Again a great confidence builder and will increase the chances of getting something that suits you.

In general, as others have said, be confident. Initially you'll be as nervous as hell. This will quickly pass. If shopping, talk to the cashier, same for those waiting on table. Engaging with folks will again boost your confidence.

I would also say have some sort of plan, a timetable. Look up if there are wig salons where you're going. Ring ahead to see if they deal with our community and also, if their Web site doesn't give prices, ask. I was going to visit one and saved myself a wasted trip as their prices were above my limit.

If your trip is anywhere near those I've been on you'll have a wonderful time but be warned, it's addictive. Once is never enough.

[Rhonda Jean]

I've done it. One of the big things for me that you didn't mention is shaving. If I'm going to be out all day and into the night I need to shave after about 4-5 hours. Necessary, but an extreme buzzkill. In the morning I'd use a blade and then an electric. The second shave I'd do electric only. It absolutely sucks to take makeup off to shave.

As someone else said, no mini skirt. Wear what other women will be wearing. Take your cues from your wife. Not cool to wear a miniskirt and heels if she's not, and probably not even if she is.

Don't dress like a crossdresser. Dress like a woman.

[kimdl93]

Good advice on the clothes, but sherry gave the best advice. This is a vacation with you wife, and while its amazing to share it with her, en femme, try to make this experience great for her. I would start by getting her involved in all the wardrobe choices, doing your makeup (some will help), and choosing activities/venues.

[TheHiddenMe]

I have figured out that I'm not very good at eye makeup and if anyone is close enough to see eye makeup they have probably figured out who I am, so it doesn't make a difference. I'd suggest not worrying about it and save yourself time and headaches.

Second, give yourself at least an hour to get ready. Guy me is five minutes. Girl me is a lot longer, including shaving closer, makeup, putting on intimates, etc. It just takes longer.

As to miniskirts, I'm in the wear what you want to wear camp. You may have great legs for a mini-skirt.

If you are going to do a lot of walking, avoid walking in heels. Wear something comfortable to walk in, and when you get to where you're going, pull the heels out of the bag you were carrying them in and put on the heels. I've done this often.

[Jillcder]

You lucky girl this is a fantasy of mine to travel out of town on vacation with my wonderful wife wearing only womens clothing with no male clothes packed at all. Enjoy your trip and please share the details when you get back.

[jjjjohanne]

Stray thought from left field: You also have the option to wear pretty clothes, but stay a guy some days. Just an idea... :) I never present female and I'm happy enough.
I know that some people need to be 100% or 0%. So disregard me as you see fit. :)

Joey

[Aka_Donna]

Interesting. The thinking about it and exploring possibilities may be as great as the event. Some learnings last night.

Five days is too long, probably have to be three or four as most. We just can't stand that long in one place that is not home and get bored.

Swapping out earrings is interesting and difficult. Did I say difficult? Change from studs to drops was a piece of cake, but getting the left stud back in was impossible. After seven minutes of struggling, I had to ask for help. Annoying. Oh and unlike what I imagined, wearing drops was different. I didn't feel them when sitting, but they were fabulous when walking.

Outfit that didnot work: patterned leggings with a tunic. It was just too weird. So tonight I'm going to try solid black leggngs. Much much warmer than stockings. Almost too warm.

Found a bunch of interesting fem reading glasses to help the look. Going to play game of which do you think would look better this week.

Wig planning is sometime today. Only have two cheap paula young wigs. One has too much copper in it and looks horrible with skin tone. Other is a blonde, but looks like cheap wig and not hair. No good wig stores with 40 min drive, so may just try crossing fingers and ordering online. I used to have a great wig used for a birthday party, but no one can find it and I can't find it on line.

that's it for today. Just a bunch of fyi info. Hope some of it is amusing.

[Cheryl T]

We did that some dozen years ago.
I packed nothing but my femme clothes and did my nails before we left. I resolved that I was going to be 24/7 for the week of the trip.
Sure it was scary at first, but by day two I didn't care anymore. We went everywhere and did everything as two women on vacation and it was awesome.

Yes, you probably need a coat. If you don't have one, maybe borrow one from your wife. If not the right size then you'll have to get one.
As for walking in heels all day. Why? Women don't do that anymore. Save that for at night with a pretty dress and going out to a nice restaurant. Wear flats, or sneakers or a small wedge during the day and be like all the other gals.
Glasses are glasses. There are so many styles these days just wear what you have unless they are really, really male.

Don't over think things. Relax and be you.

[Sandi Beech]

Hey SirDonna,

Lots of good suggestions so far. One thing I might add is this. Some are in the light makeup camp. I am not because I go clubbing but I understand light makeup is more appropriate for everyday wear. Even so take notice the next time you are out and about as to how many women wear false eyelashes. Quite a few women wear them even with relatively light makeup. They really make your eyes pop in a way you are likely to never obtain with mascara unless you were blessed with great lashes to begin with.

It does take some practice though, so if you have not given them a try you will want to start practicing now. I always use them as they really transform the eyes.

My 2 cents worth. Good luck with your outing.

Sandi

[Cheryl T]

When we did our vacation the most difficult part for me was the daily shaving. Trying to make it last all day with a very close shave took a toll on my skin. Bring a good moisturizer for under your makeup and for at night.

[Geena75]

I just got to spend three days away as Geena, never having done more than a few hours at a time before. Thank heavens I was meeting with a friend who was familiar with makeup.

I would suggest you take the time beforehand to get a makeover and tell them you want to learn. Between my friend and the makeup artist I learned about 10x more about it.

Go with comfort clothes, especially shoes. Think ahead of where you want to go or do and what outfit would go well there. I took a lot of outfits, but only used three for going out.

And following: RELAX!

[Debbie Denier]

As your wife is going with you, she wont want to be embarrassed. Trust her and heed her advice.

[Emily in the south]

Some very good advice from the experienced ladies. Some of which, I accidentally followed on my recent trip before I got to read this most helpful thread tonight, lol.
For me, four days was not enough. Just plan your days, make the most of them, relax and enjoy the time away with your wife. I would have loved to have a traveling companion.
I'm in Sun Dee's camp for sure. Great advice on the heels.

Emily

[Krisi]

I would think your wife would be able to help you with your makeup or even do it for you.

Unless you are unusually short for a man, I would suggest flats for shoes, especially in the daytime or casual places or events. Heels will just make you taller and more noticeable.

The more time you spend before your trip fully dressed as a woman (with wig, boobs, hip and butt padding, etc., the more natural this will feel when you are out in public.

Lastly, I envy you. I wish my wife would consent to go out with me as Krisi.

[Just Dana]

Hi Donna,

Check out blue light glasses. They're for cutting eye strain if you stare at a computer all day, but don't magnify or change anything. Depending on your eyes, they may fit the bill a lot better than reading glasses. For ME, reading glasses would be great for looking at a menu, but I couldn't walk around looking through them!

As pretty much everyone else said, comfy shoes! And make sure they're comfy for the long haul. A few days ago I wore my new, very cute, low top Chucks to a concert (in boy mode). Big mistake! They're fine around the house, but four hours of standing about did me in.

Have fun!
Dana