First Shopping

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.

“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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  1. Profile photo of Kelliann Tgurl
    Kelliann Tgurl 14 hours ago

    Thank you

  2. Janine 4 days ago

    My first time shopping en femme was at a Macy’s near where I live.
    I parked my car and went into the rear entrance thinking that it wouldn’t be as crowded as the front one.
    As soon as I opened the door I realized that I was going into the women’s lingerie department right in front of me.
    There I was surrounded by the most lingerie
    that I’d ever seen
    This wasn’t what I’d expected to see and I was a little overwhelmed.
    Trying not to show that I was a little embarrassed I walked past that department and went to the junior department where I knew from experience that many of the clothes in this department would fit me
    I was looking at a rack of skirts and found one that I liked.
    Taking it with me I went over to where the fitting rooms were and the lady there told me to use any fitting room that had a open door.
    I found one and went in and closed and locked the door.
    It removed my skirt that I’d been wearing and put the skirt I had found on.
    Looking at myself in all the mirrors I could see that it fit me and the length was fine.
    I took it off and put my skirt back on then went out to the checkout counter and paid for it.
    Taking my purchase with me I went back to the, lingerie department and out of the back door out to my car.
    Since then I’ve gone shopping for just about anything you can imagine and each time it gets easier for me
    I’ve even had a makeover at the same store with a new sense of how to apply makeup so that I can pass as a female easier
    Once you have the courage to venture out and try new things it really makes it easier to achieve what we get dressed up for
    Thanks for letting me tell you about my first time shopping
    Janine

  3. Profile photo of Desiree Ford
    Desiree Ford 5 days ago

    I did my first shopping ever. It was at Goodwill. I bought couple pairs men’s shorts and a lacy white top. At the register, the clerk held up the top and looked me. “This will look SO cute on you!”,she said. Everybody in line heard her. I smiled and said thank you. The ladies behind and in front of all looked at me smiling. That’s the happiest that I’ve been in a long time! I am a truck driver and have a nice gray and white goatee that I don’t ever plan getting rid of.
    My partner hasn’t made up her mind yet if she is okay with this or not . Time will tell.

  4. Profile photo of Desiree Ford
    Desiree Ford 5 days ago

    I did my first shopping ever. It was at Goodwill. I bought couple pairs men’s shorts and lacy white . At the register, the clerk held up the top and looked me. “This will SO cute you!”,she said. Everybody in line heard her. I smiled and said thank you. The ladies behind and in front of all looked me smiling. That’s the happiest that I’ve been in a long time! My partner hasn’t made up her mind yet if she is okay with this or not . Time will tell.

  5. Profile photo of jill Hoover
    jill Hoover 1 week ago

    Hi, i love wearing lingerie, can’t wear enough

  6. Katherine 1 week ago

    Thank you for this wonderfully candid (and hilarious) account of a shopping expedition. I really chuckled as I’ve been through every nervous motion and reaction you recount myself.
    Regards, Katherine.

  7. Claude 2 weeks ago

    Often we are our worst ennemy to be happy. Being scare about other people think and most of them don’t even think. Yesterday i went to a store where they shell family clothing ans buy an evening dress. The saleswoman was pretty old so when i said to the lady i was in transition’ she agree saying i Stuart with Adam et Ève…

    • Profile photo of Evie David Marks Author
      Evie David Marks 1 week ago

      Thanks Catherine, what are some of your tips or tricks for buying Femme clothes?
      Hugs

    • Profile photo of Evie David Marks Author
      Evie David Marks 1 week ago

      Courageous… but really we shouldn’t have to be afraid
      Hugs

  8. Profile photo of
    ConnieLynn Daunier 2 weeks ago

    i cannot relate to this article much. I have bought my own lingerie and other clothes since i was 12 and had a paper route…

    But i do understand about avoiding boutiques and such. them places are crazy and WAY over priced.

    • Profile photo of Evie David Marks Author
      Evie David Marks 1 week ago

      Hi Connie,
      Well its commendable that you didn’t hesitate to get the he things you wanted… starting early and self funded. Did you ever have to explain where that paper route $$ was going?
      Hugs

  9. Profile photo of Jacquie
    Jacquie 2 weeks ago

    “I grabbed the skirt, hid it under the coat which I held over my arm . . .”
    Luckily whoever saw you didn’t think you were shoplifting!
    Jacquie

    • Profile photo of Evie David Marks Author
      Evie David Marks 1 week ago

      Hi Connie,
      Well its commendable that you didn’t hesitate to get the he things you wanted… starting early and self funded. Did you ever have to explain where that paper route $$ was going?
      Hugs

  10. Profile photo of Terrim
    Terrim 2 weeks ago

    I went to my first CD party in 1978 or 9. I wore a dress that I had bought in a thrift shop. I remember how nervous I was when I bought it. After I bought it I felt so proud of myself and began to think what was I so afraid of ?.
    Each time after that I became less nervous. Then came the first time I shopped enfemme. I think I went to a department store and went a cosmetic counter. I had practiced with makeup at home and had gotten pretty good. I remember how nice the woman was. It made feel so good. I remember one time, a long time ago, I had a store security person follow me while I was shopping. I was nervous but I knew nothing could happen. Shopping gets easier each time you do it. I shop a town away from where I live. Just try to remember you are not doing anything wrong and just enjoy. I am making it sound easy I know, but just relax and you will have a good time.
    Yours Terri

  11. Danika 2 weeks ago

    I really loved your story. When I have gone to stores to purchase skirts, pants, tops or dresses it doesn’t phase me at all anymore. Many many times I have gone into the stores to buy something for my wife and never thought about where I was so why should it be any different buying something for myself. At Macy’s one time in the dress department I did have a SA ask me if I needed any help or if there was something I would like to try on but I told her that I was just shopping. I find that SA’s tend to be VERY helpful. However, once in Victoria’s Secret I was with my wife and found some nice panties on sale. In the past my wife would always take my stuff and pay for it but this time when we were checking out, I handed the SA the panties and when she rung them up, I looked at my wife kind of expecting her to pay for them but instead she said to me that as long as they were mine that I should pay for them myself. She didn’t whisper it either but said it in a normal voice and everyone around us heard her. It was at that moment that I really realize who I was and that any concerns I had about being transgender had suddenly gone away. I had found that just being yourself is all it takes to enjoy your shopping experience. So have some fun.

  12. Profile photo of Lea
    Lea 2 weeks ago

    Evie, I really enjoyed your story and it made me smile, giggle, laugh, and remind me of those first shopping experiences.

    I like the “Mission Impossible” reference – covert crossdressers have to do so much planning to avoid suspicion, detection, confrontation, and humiliation.

    I have learned though, that salespeople (especially women) easily forget that I’m a man buying a dress or heels if I engage them in conversation. I guess it distracts them, puts them at ease.

    • Profile photo of Evie David Marks Author
      Evie David Marks 2 weeks ago

      Thanks Lea,
      Back in the day, I was crazy with fear and obviously had a poor opinion of what I was doing. I wish I had The nerve to use your approach which is very commendable. You turn what could be a scary situation into a friendly interaction.
      Hugs

  13. Profile photo of debbie
    debbie 2 weeks ago

    Great writing Evie I laughed my ass off

  14. Profile photo of Veronica
    Veronica 2 weeks ago

    I enjoyed your story- it brought back some awkward but funny shopping moments of my own.

    Veronica

  15. Profile photo of Jillian Simpson
    Jillian Simpson 2 weeks ago

    I love this story. Soo true

  16. Profile photo of skippy1965(Cynthia)
    skippy1965(Cynthia) 2 weeks ago

    Very nice telling of first time shopping experience! Thanks for sharing Evie!
    Cyn

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