First time out for multiple days (maybe)

[Sherry Ann Evans]

My wife is traveling for a week in May, so she suggested that it's a great time for me to also do some solo travel and finally fulfill my dream of being Sherry for more than just one day. :)

I decided to go to Boston. I went to college there and feel very comfortable in/around the city. I know my way around, what are the safe areas, etc.

So ... Sherry is taking a vacation!! I''m so excited. I've been out dressed many times, but never for longer than just one day/night. The biiiiiiiiiiig question is, do I also take a set of male clothes, just in case? The rational part of my brain says, duh, of course I should. It's for safety. But my heart says, no don't do it, because then it would be too easy to wimp out of dressing each day. I'm excited about the fantasy of * having * to be Sherry, or else I can't leave the hotel room. :) Will I regret it, that's the question.

PS. I live within one day's drive (about 5 hours), so no flying/security is involved.

[Bluesman]

Go for broke! No male clothes.:)

[Rhonda Darling]

I agree with Bluesman, don't take any male clothes. Take a walk on the wild side. Flying w/o a safety net builds character and confidence. When you can't change, and you've got to pee, you will expand your comfort level. Trust me, it's exhilarating.

[Susan_Michaela]

I third the motion. Enough said enjoy have fun live your life one day at
A time.

[Kris Burton]

Three simple words Sherry - Go for it - and be sure to tell us how it went!

[TheHiddenMe]

I've done out of town trips and the only boy clothes I took were my workout clothes.

Get your fingernails done at a salon. That makes you more "pot committed" to use the poker term.

Push come to shove, you can always hit a store to buy boy clothes--as Sherry of course. Easier for a woman to buy boy clothes than vice versa.

[Helen_Highwater]

If you've read any of my posts you'll know once a year I spend 7 days enfemme, 24/7.

I do take drab clothes, leaving the house dressed is problematic hence I end up with the very basic male clothes by default.

That said I change in the car once away from home and that's the last I see of them until the return journey.

Being enfemme continuously is wonderful but be warned there are issues. Close shaving everyday can take it's toll. Putting makeup on and then cleaning up before bed can become a chore. Footwear, wearing even kitten heels can be punishing on feet and legs only use to a few hours wear.

As you've been out before I'm assuming you're comfortable using the ladies facilities, dining out in public, all those sort of things add to the overall experience and even if you have drab with you, once you get going the desire to do yet more will be your driving force.

Enjoy your trip, live life to the full.

[Emily in the south]

I drive that distance regularly in girl mode & take no male clothes for multiple day trips.
Like Helen, I need to be careful leaving my house during the daytime. I underdress with girl jeans covering leggings & a oversize sweatshirt covering a top. A few miles from the house, I transform in the car, removing the jeans & sweatshirt, switching running shoes to ballet flats I keep in the car. Add wig & jewelry and voila.. I'm back on the road.

I suppose a factor is your car reliability. So my gv jeans & the sweatshirt might come into play should some disaster happen. I never wear them on trips, they just stay in the car for when I return and get close to home.

Another vote to go for it. You will have no regrets.

Emily

[kimdl93]

There are no rules. Just guidelines. If you have a pair of sneakers, jeans and a sweatshirt in the trunk of your car, you?ve got your backup. Enjoy the experience.

[JulieC]

If you've been out dressed many times, then there really isn't a reason to have some male clothes along with you, is there? :) Plus, it will prevent any chicken-out moments. If you do take them and have a chicken-out moment, I'd be that after the trip you'd be kicking yourself for having chickened out. You're going to a place you know. You know how to be safe. What's to lose? Go for it 100%. How many opportunities are you going to have to do this?

[Sherry Ann Evans]

Get your fingernails done at a salon. That makes you more "pot committed" to use the poker term.

Push come to shove, you can always hit a store to buy boy clothes--as Sherry of course. Easier for a woman to buy boy clothes than vice versa.

I was thinking about that (nails). I've never had them professionally done, so that would be another fun milestone. :)

Good point about clothes shopping, if necesssary,

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If you've read any of my posts you'll know once a year I spend 7 days enfemme, 24/7.

I do take drab clothes, leaving the house dressed is problematic hence I end up with the very basic male clothes by default.

That said I change in the car once away from home and that's the last I see of them until the return journey.

Being enfemme continuously is wonderful but be warned there are issues. Close shaving everyday can take it's toll. Putting makeup on and then cleaning up before bed can become a chore. Footwear, wearing even kitten heels can be punishing on feet and legs only use to a few hours wear.

As you've been out before I'm assuming you're comfortable using the ladies facilities, dining out in public, all those sort of things add to the overall experience and even if you have drab with you, once you get going the desire to do yet more will be your driving force.

Enjoy your trip, live life to the full.

I'm fortunate that I can come/go from home without any issue, since my wife is supportive and my car is always parked in our garage.

Daily close shaving is definitely a concern. In drab life, I have a beard most of the time, and only shave all the way when I want to dress up, which is once a month or so. Suddenly going from that to daily shaving my wreak havoc on my face.]

Shoe-wise, I tend to go with pairs that are comfy vs. purely sexy. I only wear heels if they're chunky, for example.

- - - Updated - - -


If you have a pair of sneakers, jeans and a sweatshirt in the trunk of your car, you've got your backup.

Another good point. Thanks! .... If they're just in the back of my car, and my car is in a garage at the hotel, then I'd still have to dress up to go retrieve them .... in which case I'm dressed anyway, so I might as well stay that way!

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If you've been out dressed many times, then there really isn't a reason to have some male clothes along with you, is there? :) Plus, it will prevent any chicken-out moments. If you do take them and have a chicken-out moment, I'd be that after the trip you'd be kicking yourself for having chickened out. You're going to a place you know. You know how to be safe. What's to lose? Go for it 100%. How many opportunities are you going to have to do this?

That's the gist of it! Trying to pysch myself up for it. :) May should be nice weather, too.

[kimdl93]

The subject of getting nails done brings back a wonderful memory. Many years ago, when I spent my first extended period dressed (13 days) I began it with getting acrylic nails. It was a commitment. After I did that I realized that I had planned to have an informal meeting with a business colleague the following morning. Rather than ruin the new acrylics I opted to attend in girl mode, wearing in a cute peach 3/4 sleeve sweater and white knit skirt. The woman I met with was just a bit surprised, but very welcoming and encouraging. It went so well that later that day I called up a GG friend to invite her out for lunch?she instead invited me to her house. We spent the afternoon visiting. It was lovely.

[Sherry Ann Evans]

Awesome!

I'll need to learn more about having nails done, before I set foot in the salon. I wore cheap fake nails once or twice (not enjoyable) and simply painted my real nails a few times (so much more satisfying). I wouldn't want anything that is too hard to remove, or too long. After all it's only for a few days and I still need to function! But I think just getting them professionally painted would be great, maybe with a cute design on them.

[oh to be rachel]

I just spent 15 minutes down a rabbit hole looking for pictures of my nails when I had them done. I can't find 'em. Sorry.

Have them professionally done! At least once. The amount of pampering is awesome and it will teach you how to do them on your own (or at least what they should look like).

And get your toes done too!

By the time you'd spent all that money on them you'll commit to keeping them painted for a week or so.

[Sherry Ann Evans]

Definitely toes! :)

I'm going away for four days, and then the next day I have to return to my job in 100% drab, so I can't keep my fingernails done.

[Genifer Teal]

When is this? I know some people in the neighborhood that could show you the way around.
You can always PM me if you don't want to announce publicly when you're going.

[Sherry Ann Evans]

I don't mind saying, I am going May 4-7. But I will send you a message.

[Sometimes Steffi]

I've gotten my nails done many times, at many different salons.

I used to get my nails done when going to the Keystone Conference. One time I got dipping nails. They were about 3/4 of an inch over my fingers. At first, they were really hard to do just about anything, but eventually, they felt more or less comfortable. They were really awesome. Just remember, you can't do DYI to get them off. The need to be taken off using an acetone soak, and then some pealing and buffing. Still, totally worth the experience.

[Sherry Ann Evans]

Steffi, what do you recommend for me? I want something short (functional!), easy to undo, but still very pretty and feminine.

[Jillcder]

Absolutely no male clothes Sherry! As a crossdresser there is nothing more exciting than to be away from home with no male backup clothing. Enjoy your girl vacation.

[Sherry Ann Evans]

Jill, I've been away from home and fully dressed many times (never needed 'backup clothes'), what's different this time is just one day/night vs. an extended trip.

[Sherry Ann Evans]

I soooo appreciate everyone's supportive comments -- thank you!

My trip isn't for another 2.5 months but I'm already super excited. Originally I was thinking about leaving home dressed, and just leaving drab life behind for a few days. Maybe instead it would be fun to leave home in drab, change at my hotel, and then throw away the male clothes when I get there, leaving me stuck. ;) But then I wouldn't have the joy of checking in as Sherry. Decisions, decisions!!

[Sometimes Steffi]

Steffi, what do you recommend for me? I want something short (functional!), easy to undo, but still very pretty and feminine.

Sherry Ann

If you want something that's easy to get off, even if you want to take it off DIY, just get regular nail polish. Gel nail polish is more difficult to remove that regular nail polish, and you might not be able to get it off DIY. Acrylic and dipping nails are more permanent and definitely not DYI.

At a nail salon, a manicure consists of a (clear) base coat, two color coats and a (shiny) top coat.

I can usually grow my own nails reasonably longish, so that they can easily pass for feminine. However, no matter how hard I try, one or two nails break, usually right before the event, and the nails end up being of uneven length. The Nail Techs usually prefer perfection, and the will file all nails down to the same length, meaning the shortest length. I ask (tell) the NT to keep them long and to only file for shape. You may want to look up the various nails styles. Typically, round, almond or oval are best for short nails. Another alternative is square nails; these are definitely femme.

Even if you have short (typical length boy) nails, you can still get a very nice manicure. Feel free to pick a wild color, like red, hot pink or purple. Or go really wild and get ocean blue. You can also get sparkly nail polish or a sparkly top coat.

I will try to attach some of my pics.

Oops. My pics are all on my other PC or on my phone.

[GraceH]

This will be a fun adventure, Sherry. I'm rooting for you. I've done a few trips like this and one of the more interesting parts is checking into a hotel dressed, and having to present your (male) ID. I just tell them to call me by my femme name, and when I check out, that's what they use. Get that manicure and a pedicure, too-- the pampering is wonderful, and looking down at your nails for those few days is always a fun reminder of where you are and what you are doing. Acetone takes off regular polish in minutes, so if you get regular polish, you won't have any trouble transitioning back to male mode. I use cotton balls and soak them with the acetone-- polish comes right off. It smells pretty bad, so I toss them into the fireplace and light them-- the odor and cotton balls disappear in seconds. Have a great time!

[rachelatshop]

Hi Sherry, I'm Rach and live in Maine and have always wanted to venture to the Boston area to have a true outing. Are there a lot of safe LGTBQ areas and are there any make over places. Thanks you can DM me if you would like. Have a great time Hugs Rach

[Sherry Ann Evans]

Yes! I'll send you a message soon.