Personal Shopper, or My Fourth Public Outing

by Ashlee

  

This is an autobiographical work of non-fiction. Everything described here, in all detail, is true, as in my earlier accounts. I will say that I have had some twelve public outings, most unremarkable aside from a disbelieving laugh. This I include as the first to go a couple steps further (still far from the assertion and confidence of those who live across gender lines every day). The two may interest only me...and the five people who saw it. I will also say to the two other principals here...I apologize for my dishonesty. Perhaps it was unnecessary in which case what a missed opportunity.

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A Deb? Outside? What? (Note to the dear reader: "Deb" is the name of a clothing store that caters to teens and young women.) Outdoor malls, so-called "lifestyle" malls are supposedly gaining ground, even here in snowy New England. Apparently people feel that shopping is less a soul-deadening experience if it's interrupted by bouts of cold, heat, or rain. Or as in today's case, a February snowstorm.

But I never would have expected a quintessential teenybopper mall store, Deb, to be attached to an outdoor mall. My carefully conceived plan was dependent on an indoor mall, but I wasn't about to scrap everything after having driven 45 minutes from home.

Popping into stores to buy something en femme was still a thrill, but like all thrills familiarity breeds contempt. So it was time once again to step it up in this battle for "safe unpredictability". On the safe side, it was 10 in the morning, which doesn't attract too many shoppers on a weekday. On the unpredictable side, here I was.

At this point I usually describe in detail what I was wearing. Well, here it is: a grey male t-shirt, male boxers, male jeans, along with black socks and boots made for a man. So how is this about crossdressing you ask? You'll see soon enough.

I chose Deb for its bent toward trendy clothing – stuff popular among teenagers that will be 60% off in two months once the novelty wears out. Deb's offerings were perfect for "Ashlee", my femme persona. She is a young teenager, 14ish - flirty, silly, gossipy; the epitome of the boy-crazy cheerleader.

So I enter Deb right after 10, so early the pounding music isn't even on. There are two young women, probably both college age behind the desk, and I get the expected "Hi, can I help you?" I replied that yes I could be helped. I stumbled for words, explaining that I was looking for a top...for me. After a couple failed attempts at elaboration, I took out a note that I'd earlier written in my most feminine penmanship, and handed it to them to read. It said in its entirety, complete with poor English:

= go to deb

= ask the girl there to pick the most embarasing top there and two acessories a purse mebbe. Spend like $40 dollars

= change into the stuff there and throw out your old shirt

= ask the salesgirl if you can buy her coffee or sumthing for helping you

= walk around the mall in your cute outfit till you find us!

As you can see, that last item which would have set me up for a great deal of humiliation inside the mall no longer applied. The rest, though, did. It seems the note, in its girlish handwriting, had an air of authenticity while also granting tacit permission to treat the customer as victim. At least, that's what I was aiming for and I did okay enough.

The older girl, the manager, read this, entirely credulous before tilting it for the other's consideration. The only reaction I got was a stunned "and you agreed to this?". I explained that this was the cost of a bet, and that I had fully expected the Patriots to win the Super Bowl. (As did nearly everyone, including these ladies.)

The two moved behind the counter in the still silent store, and looked at each other for a moment. The manager said to the other "I'm thinking I'm the hot friend?" Before a reply could be offered, the younger answered the phone and was out of the picture for a while.

**outfit.jpg**

The manager bade me to come with her, and we shortly arrived at a rack, and she pulled off a shirt, "What do you think of this one? It's pink and it's sparkly." Indeed it was. It was a medium pink short-sleeved shirt, with the words "I'm the HOT friend" taking up three rows across the front in letters 2 inches high. The letters graduated from a light pink up top through a yellow to blue at the bottom, and were covered in sparkling glitter that shed easily (see attached photo).

Now, I knew that I'd seen "my boyfriend is cuter than yours" on the way in, but figured it would be a bit odd to point that out. So I merely shrugged with a sheepish grin, assuring that it was up to her. In what may have been a first for her, the manager literally sized up the man in front of her.

"I'm going to give you the largest one to try on. No offense." So off I went to try on the shirt in the dressing room. The manager returned to her post, trusting that I could figure out if it fit. I returned later (wearing my old shirt) and confirmed that I guess it did, though the shirt felt a bit short and tight. I was assured this was normal.

At this point the younger one again pointed out the need for accessories. They chose quite a purse, a largish pink foil one with a shoulder strap; if nothing else they certainly took the "embarasing" part to heart. We learned that my hand wouldn't fit through the matching bangles, so we settled for a long beaded necklace. As one girl pointed out so helpfully, it matched my purse! The other chimed in that hey at least I wasn't going to be wearing a corset.

I was rung up for under $30, not least of all because they kindly chose stuff that had been on clearance. As the manager chirped "this shirt works, because you have to find your friends in the mall, and you'll be hot, so you'll be the hot friend!"

In the end, my offer for coffee was declined as neither of them drank it, and once I changed into the new outfit I was done. Oddly, neither stuck around to see me in the outfit they'd chosen, though three customers entering the store did. I just grinned at them and said "long story" as I walked past holding "my" purse, passing a rack with deep discount winter jackets, and out the door...

...Out the door into a snowstorm that had even worsened in intensity. That's when I got a second idea. I went to a nearby store (in my male jacket), and purchased a girl's winter jacket, toque (or wool hat), gloves and scarf. The jacket was again trendy for teens, with a deep hood lined with grey faux fur, and a print of rainbow-colored glittering jewels on bright white. The jacket didn't even come down to my waist. A pink scarf, white gloves, and pink hat completed the outfit.

So I return to my car, changing from my jeans into white capri pants with a pink sequined belt. I also slipped on a bra with some water balloons underneath before pulling the shirt over. With a bad wig topped by the cap then the hood, rather good eye makeup, and the scarf and mittens, I was ready to go.

So out I went for a half-hour walk, my male telltale body hair and bone structure well-covered. Hundreds of cars went past on the main drag where I took my stroll, as did some 10 or 12 pedestrians. And there I was, head-to-toe in female clothing in broad daylight, wearing a jacket and belt, and carrying a purse all meant to catch the eye. This is the most watered-down version of "passing" but I did it. The best moment being at a crosswalk, when a truck stopped to let me cross as I focused on swaying my hips just right.

All in all, it was a lovely New England day.

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I do regret that it was an outdoor mall and should I try this again I'll make sure that I visit an indoor mall instead. There is the ever-present tension whereby sales staff -– in some ways a subservient relationship –- are encouraged to take more control. The girls obviously enjoyed my discomfort, but also didn't want to take it too far. In an indoor mall, other customers and staff wouldn't have felt so restricted, and there I'd have been in a fairly unsubtle shirt and purse, an easy target.

Will there be others? Who knows. I think I'm truly pushing the limits that are set for one person who doesn't want to be too confrontational or push others far outside their comfort zone. Possibilities could open if I entered an explicitly t-friendly zone or met up with someone willing to serve as guide or orchestrator of my humiliations. But as long as I'm more or less alone in this, I can't imagine it getting much better...but one never knows.

I'm open to reactions, praise, condemnation, offers to save my soul, and pleas for help moving stolen millions out of Nigeria. My email is totalgirliegirl at lycos dot com and I'd love to hear from you. Thanks for reading!

  

  

  

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