Sunday, May 7, 2017

On The Road Again - Day 14 and Thoughts.

When I awoke on the morning of day 14, the train was nearing Chicago.

I shaved, cleaned up and dressed in my capris and a turtleneck as the weather was forecasted to be cold there.   One of the female servers (the one who had the discussion the previous day about guys wearing capris) hadn’t worked my table yet…so today was her first time.   And I was wearing a capri outfit (like she was discussing yesterday morning.)   She seated me at a table with a guy I had lunched with previously.   Then she seated a 30something guy and a 70something woman there with us.   What to expect – good treatment, or a nasty comment about guys in capris and lipstick?  However, I needn’t have had any concerns.  She handled everything "right out of the textbook.She took our orders “ladies first,” and I was the first lady.  (Does that signify she thought I looked OLD!?  LOL!)   Then she addressed me as “Ma’am” for the rest of the meal.  Did I "pass?"  Or was she being politically correct?  I'll never know.  But in either case, how very affirming and pleasant!

Lunch was served early, and I was seated with 3 other women traveling alone.  Everyone was friendly, and for some reason by then I felt much more comfortable in the company of women, than men.   But all too soon it was time to go back to the sleeper and prepare for an on-time arrival in Chicago.

During the layover, I knew my "nose needed powdered" so I sought out the family restroom, which the Chicago Metropolitan Lounge so conveniently provided.  And as things turned out, I could have worn a skirt on to "my wife's train" - the car attendant was young and not a regular on that route. And I didn't know any of the other passengers in the sleeper.  But you never know...

Once on "my wife's train,"  dinner was uneventful, two men and one other woman at my table.  Very nice...even dressed as I was, they presumed me to be "female."    And for breakfast the next morning, same thing.  By now it had become very routine.  And I love it...

The very last leg of the trip was a ride on the commuter train, to BWI Airport and my car.  I boarded and took two seats - one for me and one for my baggage (these commuter railcars didn't have luggage racks, but serve an airport, so what do they expect?  There were lots of us like that on the train, and at least it wasn't rush hour.)

So, who came in and sat across from me but people from my old line of work, who were part of an organization I dealt with on occasion.    This is a dreaded circumstance in which wearing a skirt and/or having red nails would have presented me with a dilemma.   I probably would have just "shut up and said nothing" to them if they didn't recognize me.  But if they did...the skirt would have been rather hard to explain (except if it were Halloween.)

I'm not sure if they presumed "girl" or "boy" when I started chatting with them across the aisle, but I guess I'll find out in due time if the man ever responds to the email he asked me to send.   If it begins "Dear Ms. Sherman:" I'll know what they thought.  (Remember, my given name has been surrendered to the girls - that may also play a part in it.)

My "hindsight" thoughts...on this wonderful experience:

This was a superb trip.  Nearly two weeks in skirts and being accepted as a woman 99% of the time, makes it hard to revert back to my normal style of dressing…even though that is not at all masculine.  So, if ever presented with another circumstance like this, what would I do differently, or try to change?

1.  For a trip of this length, a "different" spare girly outfit would have been desirable.  I didn’t wear my spare white skort with the blue floral blouse, to limit laundry complications after the trip.  And in any event, since the skirt on the skort is only on the front, and the back looks like shorts, it may not have been feminine enough.   After multiple compliments about my long red paisley skirt, it seems like more time in long skirts would have been appropriate.  Perhaps if (or when) there is a next time,  I'll pair my 3 long skirts and one knee length denim skirt, with women’s polos and tees – the ones which are part of my normal wardrobe, to ease laundry issues back home.   But I would also take an overtly feminine blouse (like the blue floral one) in case of special events.

2.   I contemplated having my newly-filled nails painted bright red before catching the train on departure day, to provide almost 2 weeks of an extra feminine cue.   But I hesitated for several reasons, not the least of which was “what happens if this turns into a disaster and I have to present as male?” 
                                                                                                                                                                                                           Completely removing regular polish from filled acrylic nails “neatly” and without tell-tale remains around the edges is not easy without professional help…and gel colors have to be removed by a nail tech.  Plus, guys don’t often wear red-polished nails.  (But without male clothes, presenting as a guy would be tough, anyway.)    Thus, hesitation was definitely the wrong long as I planned some time to get the color removed in  Chicago.     Other than stirrup pants which I wore on departure day, capris for any colder weather and returning home (and a pair of shorts for emergencies), skirts were the ideal bottoms for traveling.  I wish I could wear them more often.

3.  I was concerned about my voice becoming an issue.   Given the circumstance of complete anonymity (I’ll likely never see any of these folks again),  my voice was accepted as part of me.  Hoarseness from a slight cough gave me some perceived cover (for anyone who thought about it.  But apparently nobody did.)  I simply couldn’t maintain the softer tones I use, without my voice cracking after a few sentences.   I’m just a girl with a deep voice – until and unless I get some voice coaching.  That probably won't happen...

4.  Makeup application:  I had my complete makeup kit with me in the suitcase.   But I only used it once.  The rest of the time I used concealer, foundation, powder, and 12 hour lip color (note: it doesn’t last 12 hours), all of which I carry in my purse.  No eyeliner, eye shadow, blush and so on.  On the train, and especially while sightseeing, I wore more makeup than the other girls.  Most weren't even wearing lipstick.  I seemingly can’t escape wearing at least SOME makeup, to keep my beard shadow under control.    But “less is more.”  

If I ever transition, I’ll cross the “makeup” bridge for dressy occasions when I come to it.

5.  Shoes:   Flats worked just fine, and I wore them all the time.   Sandals weren’t comfy enough to wear all day, every day, and aren’t permitted (outside of sleeper accommodations) on trains.   Too much metal, too many pinch points down low.  High heels on the train would have been downright hazardous to remaining upright, probably resulting in falling into some poor passenger's lap.  (And, they're not much less dangerous on the cracked sidewalks of city streets.)    I need to find something comfortable with a 1 or 1-1/2” heel, and sling or closed back, for dressier days and evenings.  In retrospect, I should have taken my clogs. They at least have heels, and even without back straps to hold them on, I noticed several girls wearing them on the train.   Next time!

6.  Earrings:  My ears aren't pierced, so I have no choice but to wear clip earrings.   And I wore them almost constantly, until I got home.  (Yes, my ears ached quite a bit.   Long live aspirin.  And I moved the clips around a bit - which helped.)   On this vacation, one of my cute little pearl earrings disappeared at the Santa Monica Pier, and I didn't notice it was gone until it was too late.  :-(   But I had the foresight to bring another pair, much more dangly and sparkly.  So I started to wear these instead:

I like them - their movement can definitely be felt with every movement of my head.  If one drops off (only happened once), that should be noticed right away.   Plus, during this two-week travel period, my ears seemed to adjust quite a bit to pressure from the clips.   After all, until about 10 years ago Mom wore clip earrings all day, every day, and managed to reach 93 years of age without pierced ears...   I simply can't foresee getting mine pierced, at least in the near future.   But I "never say never."

Naturally,  I'm wondering when (or even IF) I’ll be able to try a "vacation" like this again…from looking at our calendars, it definitely won’t be this year!   And if long distance Amtrak trains end up being de-funded by the new administration…there will never be a repeat!    So I'm thankful I took the opportunity when it presented itself.   (And from the weather reports I see, it appears my timing was excellent....)

That’s all for now…


PS:  When I got home, I accidentally arrived wearing both my necklace and bracelet.   I've always wear the necklace, but it's a first for the bracelet.  Nothing was said.  One more envelope pushed successfully! (And I wore it every day the next week as well, with no comment.  Yay!)  I'm just glad I remembered to take off the earrings!


  1. Mandy
    It surely does look like you pushed the envelop in many ways on this junket. You were able to present in a skirt and makeup every day for two weeks. Going forward you may want to consider shoes with a wedge heel. They can bridge the gap and be both feminine and not so feminine.
    With us it really is about pressing the envelop and helping our wives feel safe and loved regardless of our sartorial choices. Saturday after golf I was tired and I went down to the basement to watch the Ranger game and then the Kentucky Derby. The Rangers are breaking my heart with their overtime and late game gaffs but during intermission I would switch to the Derby and admire all the dresses and hats. I then changed into a floral, sleeveless, lined, knee length shift dress, complete with my bra, slip, falsies and a lovely pair of black and white 3" pumps so I cold feel some sense of communal style with the ladies at Churchill Downs.
    My wife came down and we discussed one autotrain ride when we had dinner with two 'southern ladies' who were discussing their need to get going on purchasing their Derby day dresses. At that meal I know my wife knew that my faked indifference to the conversation really was an act and that I would have loved to have 'shown my cards' and joined in the discussion of getting a special Derby dress and hat.
    Sunday she had a lunch to attend with some of her old college friends. When she got home I was down in the basement partially asleep in the chair wearing a blue knee length shirtdress with 3" purple suede heels, full makeup and clip on earrings switching back and forth between the golf match and the hockey game.
    Later in the afternoon we discussed doing a cross country train ride as two women, at least for part of the run.
    For dinner we decided on take out and she suggested I use her makeup removal pads before changing. I only partially changed into slacks and a polo while leaving my undergarments in place, complete with my falsies.
    Like you said we are continuing to press the envelop.

    1. I'm looking now for wedges on-line. If I find them in stock with a site that has brick and mortar outlets, I'll go try them on, and buy them there if they fit. Saves having to explain buying shoes...

      Sounds like you had a substantial adventure of your own...with falling asleep dressed! It's good that you could go as far as you did with dressing in your wife's presence. That's an advantage I don't have!

      I can wear my everyday feminine garb and my night dresses/night gowns, as well as panties, camisoles and stockings. Plus flats and sandals. But I don't wear skirts or daytime dresses, heels (other than clogs), most jewelry, bras/falsies or heavy makeup. That would be too much, at least for now. Maybe one day...

      Wow, a big plus was your discussion of the X-country train trip with part of it as two women! You go, girl!

      And as far as pushing that envelope: "Yes Ma'am - we do! Every chance we get!"