My Worst Nightmare Crossdressing

I was out all day Monday. (That’s me in the photo before going out.)

In the morning, I did outreach at a Human Sexuality class at Southern Connecticut State University.

After the class, the professor took us out to dine at a local New Haven eatery.

And after dining, I planned to return home. Before starting the car, I called home and discovered that my presence was not required at home as early as I had previously thought, so I had more time to spend out en femme.

I pass a DressBarn on the way home, so I decided to stop and shop.

After shopping at DressBarn, I returned to my car and it won't start! The dashboard lights up, the radio plays, but when I turn the key, all I get is a loud ticking noise.

I have AAA, but I am a little concerned about dealing with AAA en femme.

As I am sitting in my car contemplating my next move and occasionally turning the ignition key to no avail, a small red pickup truck parks next to me just as I am cranking the ignition for the umpteenth time.

Two young fellows get out of the truck. They do not ask me if I needed help. Instead the driver walks to the front of my car and signals to me to pop the hood.

I gladly do so and the two of them poke around the engine compartment, but do not find anything amiss.

I have a set of jumper cables, so we tried jump starting the car, but that does not work.

Since my car has a manual transmission, they suggested rolling the car and popping the clutch to start it. (I had not done that in years and had completely forgotten that trick.)

So they gave my car a little push. The car started rolling across the parking lot and I am trying to pop the clutch, but I am not getting the job done.

Just as I am about to run out of parking lot, I remember that I have to pop it into second gear, not first gear, and as soon as I did, the car started.

I waved my hand out the window to my two "good Samaritans" and headed straight home with my fingers crossed that nothing else would go wrong with my car.

I made it home without issue. This morning, I popped the clutch again to start the car and drove it to my dealer to get it fixed (my car needed a new battery).

I always worried about having car problems when en femme. I thought it could be the worst thing that could happen. Now I am not so sure.

Maybe it is better to be a woman than a man when car problems strike. Would those two fellows be so quick to come to the rescue of a tall middle-aged guy as they were to come to the rescue of a leggy middle-aged blond?

I don't know and I am not anxious to find out again.

(Notary Sojac: This is a redo of a 4-year-old post.)




Source: Madeleine
Wearing Madeleine.




James Ross
Professional femulator James Ross and son

7 Top Make Up Tips for Crossdressers (Male to Female Transgender / Crossdressing Tips)

1) Shave at least twice before applying makeup. A clean shave is the key to flawless makeup application. If you can’t create a nice smooth surface, you will not have a good base for makeup. If you want a professional looking finish, find a way to get rid of all the stubble. What usually works […]

The post 7 Top Make Up Tips for Crossdressers appeared first on Glamour Boutique.

Lemon Meringue Pie Crossdressing

Wednesday was going to be a very big day out en femme for me. I was going to take the train to New York City to attend a conference with my boss and her boss: three business women in The City for the day.Needless to say, I was looking forward to the tr...

Milady’s Merchandise


Jaye Anne wrote, “Maybe this will be of modest interest to our more self-conscious  sisters”

“Yesterday I went shopping at about 9:30 AM (at Walmart) and in drab, purchased three panties and a new shade of lipstick (I am partial to L'Oreal lipsticks). I checked out and paid the checkout lady, a woman of about 60. She didn't blink an eye, was friendly and wished me well.

“My point for telling this story is that people in general and women in particular don't care. They do their job and are happy for the sale.  I have, in the past, had the same experience with a skirt and blouse at Lane Bryant.”

I added my two-cents’ worth.

And if they do care, they usually keep mum because it is none of their business.

On occasion, I have had cashiers comment (always humorously) about buying stuff for milady. When they do, I tell them the purchase is for me and show them my photo en femme on my iPhone. That usually blows them away!

By the way, regarding the image above:

1) I’d like to try that while shopping in girl or boy mode, but

2) What are the health issues?

A little Googling came up with "How to Try on Cosmetic Testers in Store."

(Caveat Emptor: This is a repurposed post from 2013.)




Source: ShopBop
Wearing Theory.



Wade Barnes
Winner of the 1972 "Miss America" pageant at Bryant (AR) High School. Starla sent me this image and remarked, "His Mom looks elegantly coiffed and attired. Like mother, like son?"