Thinking like a (crossdressing) woman

[Jennifer Connolly]

As I read through all of the discussion in forums, I have often been thinking about things that I have discovered while crossdressing.  One is that if I am going to crossdress, and do it as well as I can that I need to consider things that most women have done since they were very young.  We (crossdressers) don’t have that luxury.

I have been dressing in private all my life, and want to relay an incident that happened to me with my late wife before she passed away.  We always had spent our winters in warmer climates before we moved to Florida permanently.  She was being treated for cancer at our permanent home, so periodically had to go back home for treatment.  As I have heard from many here, on those occasions when she was away, I would take the opportunity to dress with what I had accumulated and was able to hide easily.  On one occasion, I got the opportunity to dress fully except for wig and makeup.  I wanted to stay dressed as long as possible, and was completely enjoying my time dressed when I heard a knock at the door.  I was panicked, and didn’t know what to do, so I just decided to freeze, and not make any noise, so who ever it was would just go away.

Then, another knock a few minutes later.  So, I thought that one of my neighbors really needed something, so I basically ran to the bedroom to change, ( good thing I didn’t use makeup and running in heels too) and got changed as quick as possible.  I finally answered my door after my quick change, and explained to my neighbor that I was asleep.  He said that my wife had been trying to call me with no answer, and had been concerned that something had happened to me.

Then it occurred to me that, oh yeah, female clothes don’t have pockets to carry a cell phone.  So after I got in touch with my wife, I realized that if I was going to be dressing like a woman, I would need to start thinking like a woman.  I’ve since thought about self closing doors to the outside, and being locked out of my home.  That would be just one other nightmare of not thinking like a woman, when dressed.  As a male, I carry my keys with me all the time.

I was wondering if any one else has almost outed them selves by not thinking like women and forgetting things that have been thought of by women since they dress this way all the time.

I realize that some of us who are living full time and transitioning are always thinking like women, but surely you might also have a similar story to share when you first started dressing or transitioning.

 

16 users thanked author for this post.

Dani Grand, Emily, Sofie, Sarah Cerise, Robinette Robbyns, Cassie Jayson, Natalie Jones, Lauren Mugnaia, Maive O'Neal, Leah, Robyn Drake, Deborah Sullivan, Susan Talbot, Bianca Everdene, Allysa Grant

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[Sarah Cerise]

Hi Jennifer
When Sarah is at home during daylight hours there is no noise from the house, no windows open and nothing to draw any attention. We have a smart doorbell so a quick glimpse at the phone let’s me know who’s there, if it’s a courier or any other drop off people I answer it neighbours friends or relatives I’m not in.
Love Sarah xx

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Jennifer Connolly

[Cassie Jayson]

This summer I went for a walk with a GG friend at a park. I was wearing a sun dress of course no pockets. I put my car keys in a small pocket on the cover on the water bottle I was carrying. After our 20 min walk I found my car key missing. I had to call my X at our house to bring the spare key. She brought the key which turned out to have a dead battery so we had to go to a car dealer. I am soooo glad I am out to most people.

. Cassie

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Lauren Mugnaia, Jennifer Connolly

[Fiona Black]

Whenever I’m in the house I keep a bathrobe nearby so I can cover up if I have to answer the door. When home I usually don’t wear a wig & only lipstick which is quick to remove. Covering up my painted nails can get awkward sometimes.

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Robinette Robbyns, Jennifer Connolly

[Lauren Mugnaia]

Hi girls,

I have a “purse story”. I’m a full time girl and take the bus to work every day. One Monday morning I’m getting ready to go and put my hand in my coat pocket to make sure my bus pass is there…it isn’t!!
Where is my bus pass? I need to find it and quickly or I will miss my bus, I’m starting to panic!
Okay, time to think like a woman, I dump out my handbag on the bed, rummage through the contents, but no pass. Okay, guess I have to call a taxi…
Then I look up and notice my smaller shoulder purse hanging on the door handle…of course I took the bus on the weekend and the pass is in that purse. Pheww! Woman have more than one purse and we have to remember when we change the contents back and forth as we switch our purses.

Hugs,

Ms. Lauren M

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Jenifer Sexy, Michelle McQueen, Jennifer Connolly

[Jennifer Connolly]

Thanks for that Lauren, now I’ll have to wonder which purse I put things into.  Being female is harder than I thought, so much to think about.

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Lauren Mugnaia

[Bianca Everdene]

Hi Jennifer

Yes it does become clearer how women function, things most men don’t have any idea about but becomes glaringly obvious to us.
The need for a purse!

Which came first-no pockets in women’s clothing or purses? Did the fact women carry purses mean their clothing didn’t need pockets or the fact they had no pockets necessitate a purse?

Anyway a purse is now such an important part of a woman’s wardrobe. They have grown into such an important fashion accessory. Like shoes and clothes they change with the season, the fashion trend, the occasion. Love it. I now know why most women keep so much in their purse and why it can take so long to find things like a ringing phone, cash, cards keys, lippy, mascara, perfume or body spray, hairbrush, glasses, tissues, mints, and other bits and pieces depending on what we are doing,  an umbrella, tickets etc. It does allow more fitted clothing with a nice silhouette rather than more baggy men’s pants and jackets with big pockets bulging with phone, wallet, keys, tissues, and anything else we can cram in for our journey/activity.
So much fun, a journey of discovery into what it is like to be in a woman’s shoes (and purse).

B x

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Brittney Andrews, Lauren Mugnaia, Leah, Jennifer Connolly, Deborah Sullivan, Susan Talbot

[Jennifer Connolly]

How right you are Bianca, I definitely learned about a purse that day.

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Bianca Everdene, Lauren Mugnaia

[J J]

When you say “think like a woman”, do you mean irrationally?😉 That is the way my wife thinks at times.

The simple solution is to just think, it has nothing to do with being a woman or dressed. Locking yourself out of the house is just bad planning regardless of how you are dressed. As for a knock on the door, either answer it or don’t. Just because somebody knocks does not oblige us to answer it if we don’t want to. If you are made up, simply go and wash it off and the person can wait if they really want to see you. After all we are at time indisposed and we don’t have to explain ourselves. One of the  times it happened to me I just answered the door for a delivery I needed to sign for. No doubt it was not the first time for the FedEx driver. Another time I was just about to get in the shower anyway, so took my shower and the person had to wait. Had he knock one minute later I would have already been in the shower and he would have had to wait anyway.

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Lauren Mugnaia, Leah, Dani Grand, Susan Talbot

[Angela Booth]

The knock at the door is the dread when secretly dressing at home as it could be anyone.  If it is obvious you are in, music on or signs of life what happens next is the dilemma. If it is a delivery or similar they haven’t time to wait so will go away. However, such as happened to you, it could be a neighbor or family member who will persist. You were lucky that you weren’t full on with makeup and did a good get out. But what if you were fully made up? I don’t think it is about thinking like a woman but risk assessing as  a crossdresser, like you have done in hindsight. If a woman is at home she would answer the door or shout ‘I am just getting decent’ things you won’t be able to do. It’s more thinking of safety which does crossover to thinking like a woman when outside, inside is different.

I did get caught out once when I was dressed at home. The rub was that I was actually expecting someone so answered the door. The shock when I saw a neighbor there. She didn’t click and asked for ‘me’. I ushered her in and she was looking round for ‘me’ and I spilled the beans. She didn’t miss a beat and said I looked lovely and got on with the reason she had called. Phew!

Now it isn’t an issue as everyone knows and if any one calls the door gets opened, even in a nightie with a cardigan over, no makeup but always with hair with a cardigan over if the mail is early!

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Emily, Sarah Cerise, Lauren Mugnaia, Leah, Jennifer Connolly, Susan Talbot

[Jennifer Connolly]

Angela, thanks for your story and perspective.  I wish I had had a neighbor that might have understood why I was dressed like that, and without a wig and makeup, it was obviously male me in women’s clothes.  But I also knew that he knew he had to get in with the persisting knocking, so the only option for me was to bail out, and luckily I could.

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Angela Booth, Lauren Mugnaia, Leah

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