Shopping for clothes is easy for real women, but not so much for a crossdresser.  It was a major victory when I bought girl clothes for the first time.

After surreptitiously trying on some of my wife’s things to gauge my size, I drove to the mall.  From earlier observation, I knew that boutiques were to be avoided.  Their saleswomen climb all over a guy in the belief that men are incapable of finding anything on their own — too much attention for my purposes.

Specialty stores like The Gap were also off the list; the help seem too hungry for sales. Or worse (my paranoia here), they’re on the look-out for crossdressers so they can ask humiliating questions.

Stepping Out Secrets

“Are you shopping for yourself or for someone else?”

“I… uh… I’m shopping for myself. What the!? This isn’t a man’s sweater! Where are the men’s sweaters?” (Which led to browsing through men’s cardigans while gazing longingly across the store at the cute denim skirts I would gladly have died for.)

Department stores, on the other hand, are often understaffed and crowded, so I made a bee-line for JC Penney.  In the Juniors department other guys were shopping with their wives, helping them search for sizes.  I figured I could pass for one of those.

After some stealthy reconnaissance, I found just the right item — a size 13 mini by which I had walked several times.  I grabbed the skirt, hid it under the coat which I held over my arm, and then took the escalator to the Men’s department.  (I had paced out this move ahead of time. Can you hear the Mission: Impossible theme? Du-du-dada, du-du-dada.)  I paused to snag a couple pairs of jeans that I didn’t intend to buy before heading to the fitting rooms.

Jumping into the first empty stall, I leaned against the closed door, my heart pounding like I had escaped the hounds.  After catching my breath I dumped the men’s jeans in a corner and delicately laid out the skirt, a hip-looking leatherette…

I removed my pants, pleased that I’d had the forethought to wear my favorite satin panties. No BVDs for this girl!  I unzipped the skirt, wriggled into it, and turned to see myself in my full glory.

That’s when I realized something significant; there was no mirror in the stall.  The closest mirror was the three-way at the fitting room entryway which was in full view of the floor salesmen and the public at large.  Wouldn’t that make a pretty picture — a guy in a brown plaid shirt, sweat socks, and a leatherette mini doing some of those hot runway turns in the Men’s Department of JC Penny.  Sadly accepting defeat, I still had to laugh at the irony.

Judging by the feel of the skirt and what little I could see, I realized that the 13 was too big. I’d have to start over. With a sigh, it was back to the Juniors Department.  I quickly found a size 11. Repeating all the necessary moves, I returned to the Men’s dressing room.

The big moment had lost some of its glory, but at least this time there was a mirror in the stall.  I put on the skirt and struck a few poses, staring at myself in fascination.  How cute! I love it! Mmmm, this size 11 fits perfectly.  I returned to the Juniors racks and picked out several tops. My confidence boosted; I decided not to take the time to try them on.

I headed for the checkout stand, where I had to let go of the idea of a quick escape.  A mass of impatient bargain hunters crowded around, waving their purchases at the salesgirl.  As I joined the mob, I tried to carry my pretty new things in a way that would make them look more like macho sports equipment.  I found myself wishing for a backroom checkout just for crossdressers.

After an uncomfortable 15 minute wait, it was finally my turn.  I handed my squashed ball of ladies clothing to a woman behind the counter. Be gentle with me.  Nope, not today.  It was slow, torturous humiliation. She held up each item to the light, checked the tags, waved it over her head like a racing flag and sniffed it. (Okay, I imagined the last two things.)  It seemed like she was presenting each item to the crowd for their judgment.

Thankfully, the fellow patrons didn’t seem to care.  Within moments my wonderful things were hidden inside an impersonal plastic bag.  Leaving the store, I passed the Juniors racks again and froze for a moment in the glow of a gorgeous formal gown, slit up the leg and low-cut in the front.

“Oh no, not today! Haven’t you had enough?”

“No, not really. Besides, I only want to see how much it is…”

Adapted from “The Crossdresser’s Field Guide,” by Evie David Marks.

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Veronica Raines

Got a question, for whomever can answer it. I know I have to lose weight, but right now, I found out I’m a XXXL in dresses. I went to this one site, and it had some very nice dresses. But in the plus size, it gave sizes like 3XL, 4XL, 5XL. Now, what the heck does all that mean?

Terri Anne
Terri Anne

Hi Veronica, the 3xl is for Tall – a longer cut. Say a dress might be 40 ” in regular… then it may be 50 ” in a tall. These numbers are just off the top of my head.
Have you tried Catherine’s to the East side of Parkway Plaza. Across the road from Macys.
They are wonderful !! No joke.♡ – Terri Anne

Terri Anne
Terri Anne

Maybe maybe not. I’m not a good judge

Veronica Raines

Thank you, sweet lady. I’ll try out Catherine’s.

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