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My process for Planning an Outing

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Posts: 26
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Topic starter
(@Diana Stockton)
Eminent Member
Joined: 2 months ago
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I do not get out as often as I used to due the to "DADT" wife always at home, but once in a while I do get an opportunity.

Next week is the RV Expo in Indianapolis and I wanted to go. My wife wasn't interested though, so I decided I would go alone—or should I say Diana would go—and make a full day of it. I should note that my wife is not aware, to my knowledge, that I have ever gone out; she is a night owl and usually sleeps till noon, so I can dress and be out of the house before she gets up.

I spend a lot of time planning my outing: What am I going to wear is the first decision and in this particular case I want two outfits. I plan on going to the mall first, for some shopping, so I can get away with a dress. For the expo, however, I need to dress down; no women will be wearing a dress there. I figure out what underwear works for both and the clothes are done.

Next, come the accessories. My wig needs to be brushed out and I need to select what pieces of jewelry I will wear:  Earrings; bracelet; necklace; watch and rings.

I have big hands, but have found if I apply press-on nails, they help to hide their size. I color my oversize nails from Sally's Beauty Supply.  I need to make sure I have all ten fingers ready to go and some back-up nails in the case of a break or one falling off.  I keep my nails staged in a coin purse with very small baggies.  One baggie for the ten nails ready to go and five individual baggies, one for each size, labelled 1-5 for backups; I keep several sheets of adhesive tabs in here as well.

Shoes: This trip will need two pairs. Heels for the mall shopping and some flats for the expo.

Purse: I need to check the contents of the purse so that everything is ready. I keep my perfume there as I do not put it on until out of the house so that it doesn't smell. Female wallet with cash. Touch up makeup. Hair brush. Lipstick. Spare pantyhose in the case of a run. Also my women's prescription eyeglasses so I can see. At the last minute, I throw in my phone, my ridge wallet with ID and CC and my spare nail pack with adhesive and extra nails.

Makeup: I need to make sure I have enough of all my makeup. My portable lighted mirror needs to be charged. I do my makeup and dress in my home office.

Grooming: Lastly, I need to make sure my body-hair is ready. I epilate my hands but just trim my legs (Wahl 3) and arms (Wahl 1). Eyebrows are trimmed as well (Wahl 2) to keep them from being bushy.

That's the plan. Wish me luck in that everything goes well and I do not have to cancel anything. I plan on posting some pictures next week.

For those of us that cross-dress and get out, what is your process?

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37 Replies
17 Replies
Guest
(@Diana Stockton)
Joined: 2 months ago

Eminent Member
Posts: 26

i think you are overthinking it. are you going to look at RVs or taking one? i think one outfit for both would be good. do you really need extra nails? maybe 2 pairs of shoes. your going shopping and a rv show. not going for a week trip. that's just my option. 

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Baroness
(@dianas1960)
Joined: 9 years ago

Reputable Member     South Central, Indiana, United States of America
Posts: 220

@prettytoes I bought one last year but wanted to look for accessorizes.  I always prefer to wear dresses when out however I have been to the RV Expo before and noted it is a jeans event for women.  It is at a fair grounds and is a chilly venue and rough walking surfaces.  Besides being able to have 2 outfits out in a day is a crossdresser's dream isn't it.

 

P.S. Welcome to CDH

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Duchess
(@bbwmeganlynn)
Joined: 11 months ago

Trusted Member     South jersey, New Jersey, United States of America
Posts: 31

@prettytoes I dress everyday so it’s easy for me at least.I have gel nails at the moment and wore a skirt and blouse today.Being MeganLynn everyday is exactly what I need.I am going to a casino and staying over.Anyone think they will give me a hard time with ID and my credit card?
Last thing I want is to make anyone feel uncomfortable.I have a beauty routine in the am and takes me an hour to get ready.Brush out my wig,makeup and shave.Even at 51 I’ve never had much facial hair and very lucky.Try be passable(and I still don’t think I am)is so tough and expensive!

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Guest
(@Diana Stockton)
Joined: 2 months ago

Eminent Member
Posts: 26

yes trying to be totally passable is hard. as long as your comfortable people won't mind. it's hard to hide the Adams apple and the man's voice. but don't worry, people will accept you as long as you try. as far as the license goes, they are just doing there job and don't really care how you present yourself.

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(@jenniferr)
Joined: 2 years ago

Estimable Member     Greenville, South Carolina, United States of America
Posts: 81

That is so true. I think, and yes I was once one, we worry too much about being "passable". I have to accept that at my age there just ain't a whole lot I can do to change this body and face. What's there is there, been there a looong time, and has no intention of going anywhere any more. But I do dress full time, go out when and where I want, and so far have had no issues. We are who we are, and it seems as if we're happy people respond in the same manner. If we're ashamed or embarrassed, people can tell and will respond accordingly also. I enjoy going out, smile a lot, and rather than get negative feedback I get comments on how they like my nail polish or earrings or something. (Women do notice little things) Most of us aren't drag queens and don't dress as such. We dress and make up appropriately, like a normal woman would. We are who we are, we try to blend in, and for the most part (there will always be more horses asses than horses) people are quite willing to accept us as we are. As far as businesses, I've had no issues either. No matter how we dress or look, our money is still good, and I have yet to find a merchant unwilling to accept any of mine.
Hugs,
Jennifer

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Duchess
(@bbwmeganlynn)
Joined: 11 months ago

Trusted Member     South jersey, New Jersey, United States of America
Posts: 31

As far as the Adam’s apple mine isn’t very noticeable…I think?

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Baroness
(@dianas1960)
Joined: 9 years ago

Reputable Member     South Central, Indiana, United States of America
Posts: 220

Either is mine. We are lucky there.

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 Lea
Lady
(@lea-jhene)
Joined: 9 years ago

Noble Member     California, United States of America
Posts: 1103

We must be some of the world's best planners. Imagine the good we could do!!

I'm like you, lots of planning and thinking before going out. Backup shoes, backup male outfit for an emergency, never a "this old thing" look.

After many outings, I do have some outfits that are more top of mind and don't need "as much" planning.

Congrats on being bold to venture out to an RV show!! Sounds fun.

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Baroness
(@dianas1960)
Joined: 9 years ago

Reputable Member     South Central, Indiana, United States of America
Posts: 220

@lea-jhene I do also have a change of male clothes as my drab self is the one to return back home.  I am very much looking forward to having a fun day.

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Guest
(@Diana Stockton)
Joined: 2 months ago

Eminent Member
Posts: 26

i find that funny. i took a cd friend of mine out for his first time. he brought his man clothes in a bag with him. i said what are you going to do with those. he said if we get in an accident he was going to change. think about it. are you going to have time to change? are you going to get your nail polish off, make up off & change your clothes in less than 3 minutes? no. you will look funny half man and half woman. accidents will happen but changing before someone gets there probably won't. now he leaves his man clothes at home. nobody cares if you dress. police and fire people are there just to do their job.

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Baroness
(@dianas1960)
Joined: 9 years ago

Reputable Member     South Central, Indiana, United States of America
Posts: 220

It's not at the accident scene. It's how do I look when I return home to my DADT wife who does not know I go out dressed.

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(@jenniferr)
Joined: 2 years ago

Estimable Member     Greenville, South Carolina, United States of America
Posts: 81

How the fears and shame that has been programmed into us dictates how we act today. But you're correct, I go out all the time, a friend and I are going to check out a new bar tonight. I've been stopped at a road block, and one time I even stopped to ask a police man for directions. Nope, even here in the conservative south, they don't even blink an eye. Compared to what these guys see and experience on a weekly basis, we don't even register. We're not breaking any laws by being ourselves ladies, and from what I've learned about men and cross dressing over the years, the odds are pretty good that the man you're talking to, first responders too, have a few things stashed deep in some closet too.
Hugs,
Jennifer

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Baroness
(@dianas1960)
Joined: 9 years ago

Reputable Member     South Central, Indiana, United States of America
Posts: 220

I have been stopped twice while enfemme by the police. Each time there were no issues with my presentation or ID not matching it.

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Baroness
(@annaredhead)
Joined: 11 months ago

Famed Member     Cornwall, United Kingdom
Posts: 1839

I will shave, face, legs etc shower, do nails and put on a light makeup (beard concealer, mate and lipstick) and dress at home, slip male clothes and shoes on over my feminine outfit  to get past the neighbours. Drive away, stop, make adjustment to my outfit, put my wig on, feminine shoes and away I go.

I have feminine driving glasses which I will wear for the whole trip out. 

I meet a friend well away from home for a makeover, a walk and to get some outdoor time as Anna. I don't do this often.

Hugs,

Anna xx

 

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Baroness
(@dianas1960)
Joined: 9 years ago

Reputable Member     South Central, Indiana, United States of America
Posts: 220

I am fortunate to live out in the country and get get out of the house without the neighbors seeing me. I have yet to meet anyone while dressed. Maybe one day.

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Lady
(@harriette)
Joined: 2 years ago

Illustrious Member     Toronto, Ontario, Canada
Posts: 4018

You have experience going out in the wild, so you have this figured out. Enjoy your weekend.

However...

I should note that my wife is not aware, to my knowledge, that I have ever gone out; she is a night owl and usually sleeps till noon, so I can dress and be out of the house before she gets up.

The best laid plans of mice and men often go awry” is a famous line from the Scots-language poem “To a Mouse” by Robert Burns

 

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Baroness
(@dianas1960)
Joined: 9 years ago

Reputable Member     South Central, Indiana, United States of America
Posts: 220

Don't we know that. My wife was supposed to spend a week in November with friends. Trip got cancelled and Diana was bummed....

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Posts: 138
(@ajthairms)
Reputable Member     Poole, Dorset, United Kingdom
Joined: 1 year ago

Hope all goes well with your outing Diana.

My preparation for an outing...

  • The day before I usually decide on my outfit/shoes and where I'm going (either a shopping trip or a walk in a country park)
  • In the morning I have a close shave and pop on some moisturiser. If its summer then I'll give my lower legs a shave.
  • Then it is into the outfit and shoes; brush my wig a bit and put it on. I may put on some lipstick or not bother.
  • Jewellery next, usually a ring and some clip-on earrings.
  • I get my handbag ready and grab a coat if I need one.
  • Then I'm out the door and off...
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1 Reply
Baroness
(@dianas1960)
Joined: 9 years ago

Reputable Member     South Central, Indiana, United States of America
Posts: 220

@ajthairms I guess I have become a bit OCD after my retirement in 2022.  I used to dress while traveling for business as least once or twice a month.  Since then the opportunities have dried up.  I get very excited when I get the opportunity and want to enjoy the process totally.

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Posts: 3446
Hostess
(@ab123)
Illustrious Member     Surrey, United Kingdom
Joined: 5 years ago

It seems you have it all covered and hope you have a great time. Looking forward to the pictures.

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1 Reply
Baroness
(@dianas1960)
Joined: 9 years ago

Reputable Member     South Central, Indiana, United States of America
Posts: 220

I have been doing this for a very long time. I started going out regularly about 15 years ago. I will make sure to get some pictures online.

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Posts: 7833
(@aliceunderwire)
Illustrious Member     Near Burlington, Vermont, United States of America
Joined: 5 years ago

Diana,

Good luck and have fun!

Alice

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1 Reply
Baroness
(@dianas1960)
Joined: 9 years ago

Reputable Member     South Central, Indiana, United States of America
Posts: 220

Thanks Alice. It should be wonderful if all goes to plan.

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Posts: 131
Duchess
(@theapat)
Reputable Member     Massachusetts, United States of America
Joined: 1 year ago

Dear Diana,
You should sit us down on a monthly basis and make sure we all have a similar Preparedness Plan. Ignorance is bliss until leaving the safe confines of the castle. The more one thinks about it, leaving home can sure be a stomach wrenching ordeal. Just making it over the moat is worrisome alone. A bucket hat, sunglasses, and a poncho, can help. Once free of neighborhood concerns, it's all down to the other drivers, the law, and the pit-stops we need to make.

I've had it with press on nails. I find that unless they are trimmed down to 'nail biting length', routine-reflex activities are my nemesis. So I go with glue-on nails (unfinished or pre-painted) and an INSTA-DRY polish formula. If I can't apply and paint them the night before, then it's the last thing I do before I leave home. Time in the car also helps in the curing process. The only thing that could be an issue is the removal process. Leave yourself a good hour for the removal. In my final analysis, and IMMHO, the time and effort it takes me to perform emergency nail repair (and it's usually a guarantee) and the quantity and quality of 4-letter words uttered by me is beyond the scope of this letter.

Diana, I love the fact that you've provided your prescription for preparedness. Lastly, don't forget a good pair of walking/hiking shoes and a change of clothing in the trunk for that UNPLANNED EMERGENCY (Lea covered that)

Great Job, Diana.

Sincerely and With Love,

Thea

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3 Replies
Baroness
(@dianas1960)
Joined: 9 years ago

Reputable Member     South Central, Indiana, United States of America
Posts: 220

On my nails I use some Sally's Precision fit Plus size nails with adhesive tabs. I get the tabs on Amazon. It took me quite few tries to find the best ones. I too use an Insta-Dry polish, expresso is my color. I have found if I first clean my nails with alcohol then apply the tab they hold well. I lose a nail maybe one in 40 outings and have only broken one twice and always carry spares so it is easily fixed. The best part it only takes a few minutes to remove the nails and they are then reusable. Undressing time is important as I need to undress in the car before returning home.

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Duchess
(@theapat)
Joined: 1 year ago

Reputable Member     Massachusetts, United States of America
Posts: 131

@dianas1960 

Dear Diane,

If there is ONE MOST IMPORTANT THING to Preparedness and Emergency Preparedness is WHAT and WHO WE are preparing for....OURSELVES, our ability to stay calm and respond to any unexpected event, our significant others or those we hope to disguise or hide the fact of our 'other life'. I laud you for your ability to master adhesive nails. After close to 75 minutes of makeup, 20-30 minutes of adornment, my patience wears thin when it comes to nail application. You, dear lady, have accomplished what remains elusive to me. I, on the other hand, have mastered the glue-on method and, with proper planning, enjoy 3-4 days of enjoyment. As long as we obtain what we desire. Huh?

Thanks for your thorough step by step approach. Organization goes a long way to maximizing what we do.

With Love,

Thea

\

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Baroness
(@dianas1960)
Joined: 9 years ago

Reputable Member     South Central, Indiana, United States of America
Posts: 220

I have it down to about an hour after exiting the shower. Nails are the last thing I do and take less than 5 minutes to apply. Each of us has chosen a different way to enjoy our crossdressing an we are all correct for us.

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Posts: 1141
Ambassador
(@gafran)
Noble Member     Warner Robins, Georgia, United States of America
Joined: 9 months ago

You're one organized girl, Diana!
The sequence, spare parts and support systems. ✅️ ✅️ ✅️. Run like a military opp.

I wish you a happy and successful outing!

Fran 🥰

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2 Replies
Baroness
(@dianas1960)
Joined: 9 years ago

Reputable Member     South Central, Indiana, United States of America
Posts: 220

Organization was always the trait recognized on my employment reviews back in the day. 😁

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Ambassador
(@gafran)
Joined: 9 months ago

Noble Member     Warner Robins, Georgia, United States of America
Posts: 1141

Goodness I'm Miss disorganized! I argue with myself all the time about it too! It must be the girly side that wants to have her duck's in a lovely row. 🥰

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Posts: 231
Duchess
(@mkat3874)
Reputable Member     Northeast GA , Georgia, United States of America
Joined: 4 months ago

The Day before

  • Pick out my outfit and accessories. My wife helps me with this one to make sure I look as presentable as possible.
  • Clean up my eyebrows 
  • Paint my nails 
  • Get my makeup kit out and set up for the next morning 
  • Fill up my gas tank
  • Go by an ATM to get some cash on hand
  • Select my purse and get the contents situated 
  • Make sure my wig is ready to go
  • Put my emergency man stuff in the back is my car

The big day

  • Shave first with my electric razor followed by my standard razor and apply moisturizer 
  • Trim any visible nose hair 
  • Put on my makeup- my oldest daughter used to help me with some of the trickier eye products but I'm getting proficient on my own.
  • Dress and put on my accessories 
  • Add my wig and the final touches 
  • Grab my purse, keys, glasses, and my wife and hit the road for a fun day out which usually ends near midnight 

The day after 

  • Wake up late and reminisce over coffee about the previous day with my wife and start planning for our next outing. 
  • Put away all of my makeup, wig, purse, outfit, accessories, etc.
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1 Reply
Baroness
(@dianas1960)
Joined: 9 years ago

Reputable Member     South Central, Indiana, United States of America
Posts: 220

Love it. Another planner.

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Posts: 72
Duchess Annual
(@michellewayne)
Estimable Member     Seymour, Indiana, United States of America
Joined: 2 years ago

Diana, I love your organization! Well done girl! It clearly works for you and that's what matters! 

Living alone in a rural setting, I have it much easier than most. My process starts on the previous night with wig choice, clothing selection and nail color based on that choice of clothing. I paint my nails. I only shave what I know is going to be exposed. 

Next morning, change mind, sometimes multiple times on clothing and start over minus nail color. Often change wig as well. I sometimes give up and go to makeup routine, which is very similar every time. Then I seem to be calmer and find the clothing and wig. Sometimes I don't change mind, but most of the time, I do. I also pick out the shoes the previous night, but most of the time, I go for comfort and if I can get my orthotics in them, I prefer to use those shoes. 

I do take extra sneakers, in case my feet get uncomfortable. I keep extra perfume, makeup pad with foundation in zip lock bag, lipstick and powder in my purse. I keep several bobby pins and safety pins in the purse as well. 

As to wigs-I consider wind speeds if an outdoor event and go with shorter ones in higher winds. I keep spare jewelry in my vehicle as well. 

I'm impressed Diana, with going to an RV event. I would never consider this as Michelle as I don't know that I would feel comfortable there, unless with another person. I have been to this event about 15 years ago and enjoyed it.

Stay safe and happy shopping at the mall and RV show!

Michelle Wayne

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2 Replies
Baroness
(@dianas1960)
Joined: 9 years ago

Reputable Member     South Central, Indiana, United States of America
Posts: 220

Due to may DADT status I have very limited time to dress when going out. I need to be ready to go before she wakes up. I am jealous of your freedom to take your time to dress. However I do love my wife and I have to deal with both sides of me.
Last year I went to the Woodworking show at the fair grounds. That was interesting as there were not a lot of women there. I am however comfortable going out about anywhere. I was hoping to go again this year but they have cancelled the show due to vendor attendance.

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Baroness
(@dianas1960)
Joined: 9 years ago

Reputable Member     South Central, Indiana, United States of America
Posts: 220

I went yesterday and had a great time. I am trying to decide whether to document my trip in forums or an article. I did post some pictures in my private gallery. Diana also went to Harbor Freight and purchased a pipe wrench I had a coupon for.

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Posts: 353
Duchess
(@carolcorbett)
Reputable Member     WNY, New York, United States of America
Joined: 8 years ago

I’ve come to realize how important planning is. My wife has been very helpful in helping me without it because I used to bring way too much. Now I’m much more thought through it and also what could work with white so now since you can get multiple outfits out of a couple pieces of clothing great article!

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1 Reply
Baroness
(@dianas1960)
Joined: 9 years ago

Reputable Member     South Central, Indiana, United States of America
Posts: 220

Oh to have a supportive wife. Mine does not want to know anything about it. She called me out last year when she saw some clothes drying in my upstairs workshop she saw while driving up the driveway.

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