Practical considers for multi-day outing?

[Sherry Ann Evans]

Hi forum friends,

I'm looking for advice specifically from occasional crossdressers who've braved multi-day outings.

I go out dressed with my wife every few months. It's always for a day or evening, and I pass decently enough. But 99% of the time in my 'real' life, I'm a regular masculine guy.

One of my dreams is to go away for a longer time -- a weekend, or even a week -- and be dressed the whole time! Not even bring any of 'his' clothes with me, only hers.

If I do this, then what new challenges/issues should I anticipate? For example, 5:00 shadow, clothing issues, etc.?

[docrobbysherry]

When I prepare for a week long T event out of town?

I always try on every outfit with all accessories in a dress rehearsal before I go. To be sure I don't end up leaving the rite wig, heels, etc. at home!

[Shelly Preston]

I always choose daytime outfits you can mix and match.

Oh and flat shoes daytime and heels in the evening. I once had a 12 hour day in heels wow was it painful at the end.

Always have a few options for the evening depending on the venue or venues.

[kimdl93]

I never had to worry about the 5pm shadow. Lucky to be blonde and not particularly hair. I mostly pack for day time and casual wear. Its so seldom that I go out to places that might merit more formal attire.

[Emily in the south]

Myself, I always overpack, so my 5 to 7 days away are no problem with clothes. Driving to my destination allows this, if I had to fly somewhere, it would require being more selective with packing. Half the fun for me is the door to door travel fully enfemme.

All of Shellys advice is absolutely true for me. I plan my day to day outfits, which of course is affected by the season. Extra stuff, like coats & sweaters in the winter.

The big thing for me is shaving, 2 or 3 times a day. I take 2 razors with a new set of 4 blades for each. Also, a styptic pencil, a lifesaver if you nick yourself shaving.

Emily

Additionally, I take two or three wigs. One or two are always resting while wearing the other. More important in hot sweaty weather.

[Sherry Ann Evans]

Unfortunately for me the shadow is a real issue. That's why I usually go out in the morning and get home by dinner, or go out in the afternoon for the rest of the day/night. If I go someplace en femme for multiple days, then I'm not sure what to do. Would I have to return the hotel at 4:00 every day, remove all of my makeup, and reapply it all? Shave twice in a day, for several days in a row? I don't think my face (or my patient travel partner, the wife!) could take it.

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The big thing for me is shaving, 2 or 3 times a day.

That sounds torturous.

[Sometimes Steffi]

I used to have a really heavy beard. I probably needed to shave twice a day but usually didn't. But shaving very close every morning was tough on my face. I still have a heavy beard, but it doesn't grow as fast. It's also gone from dark brown to mostly gray, so it's not so visible. I also use a red cover (red lipstick is an alternative) over my "muzzle" where my beard is still the heaviest.

I take one outfit for the daytime and one for the evening. That limits how much I have to take.

Other than that, have fun!

[Emily in the south]

The shaving is not something I look forward to, but has evolved into a labor of love.
I wear very minimal makeup during the day, usually just lipstick, so the makeup removal is not an issue for me. Maybe when my makeup skill level expands, it will be more of a problem.

Wish I could commit to electrolysis..

Emily

[mykell]

hi sherry,
if you are in the area dont hesitate to drop a line.

good eateries in the area.

if you go casual you may need not change for evening events.

as far as shaving when @ keystone i would go back to the room before dinner activities and use conditioner for the shaving.
it reduced the friction and soothed the skin irritation some with the daily shaving rituals.

have fun....

[Patience]

Make sure you are able to walk average to long distances comfortably in all your shoes in different kinds of surfaces and terrain. If you can, bring a comfortable backup when going on outings. Heels can break unexpectedly.

[Helen_Highwater]

Sherry Ann,

As someone who's been doing this for some years now the thing that springs to mind is for someone new to it the routine can be tiring. Being a woman is harder than it would seem. As you say, shaving is definitely an issue. One suggestion I'd make is to consider a good electric shaver which will minimise the damage to your face. Wet shave in the mornings and then if you need a second go later in the day you can quickly remove foundation, shave again, say in the car, and reapply makeup while out and about. Do not underestimate the time spent cleaning up at the day's end. Removing makeup can take nearly as long as putting it on.

If you want to spent long periods out then comfortable shoes are a must. Heels that seem comfortable around the house can quickly turn into instruments of torture when out shopping. If you're looking to blend then look and you'll see most GG's in flats or sometimes low heels. Going out for a meal, to the cinema, to sit in a pub, is different. A short walk from the car then sitting down for the evening means higher heels are a possible choice. A chance to glam it a bit.

Skirts and blouses/tops are a good way to have different outfits by mix and match without having to take everything in your wardrobe. same skirt, different top equals different day's outfit. Two skirts plus two tops gives you four days of differing outfits.

In my early days the routine of makeup on/makeup off each day plus making sure you're outfits were suitable for the day ahead, accessorizing, just working at being as womanly as possible was draining. After a week I was ready to go back to being drab just for the rest. It does get better the more you do it but be prepared to an experience that'll be more tiring than you may first think.

Top tip; make a list of what you want to take and gather it all together ready to pack. Nothing worse that getting there and finding you've left something behind, like your forms, don't ask.

That all said it is enjoyable. The feeling of being out in the wide world all day is liberating, joyous even. Interacting with the ordinary folk, SA's bar staff, a stranger standing in the queue with you is just not to be missed. You will want more despite the fact that it can seem like hard work at first.

[Krisi]

Shaving more than once a day may be necessary. You can buy a battery powered electric shaver and keep it in your purse if necessary.