The Set-Up, or My Third Public Outing

by Ashlee

 

This is an autobiographical work of non-fiction. Everything described here, in all detail, is true, as it was in my other accounts "Buying Water as a Girl" and "DVD Night." Details that I choose not to share are clearly edited out. However, as always it occurs to me that if anyone involved recognizes this tale, the fact that they're on this site means I'd probably get positive feedback.

I hope you enjoy this account, even though it's far more pedestrian that the adventures many of you have had. I have a lot of respect for people who live openly as a member of the opposite gender and look the world square in the eye while doing it. I don't have that gumption to do that, or the circumstances to make the changes necessary to pursue this in a more strident manner. This account will bore most, but wowser was it a trip for me.

 

Section One: The Set-Up

Bumper stickers—great for telling people what to think, lousy to make your car anonymous. There's nothing like driving past the same place four times in a car with a panoply of bumper stickers to envision someone inside reaching for the phone. One might not recognize a non-descript car, but a second pass of the back of my vehicle will stick in your head.

I was driving past because I had decided it was time for another brief outing dressed as a girl, at the tender mercies of the unsuspecting. I had good visibility, as it was a little cool for August, and great skirt weather. Over my fifteen years dressing like a girl, many Internet interactions had been great and anyone I can truly say I love knows and accepts this side of me, but nothing ever beats meeting with the uninitiated.

I had driven about an hour and a half from my home in Eastern Massachusetts when I found this pizza joint in the center of a small suburban town. It was a delivery place, I'd imagine—nobody ever seemed to come in to pick up their cheesy order. After casing the joint to get a feel, I also came to believe that the employees were all women.

In my limited forays, I have noticed that women offer a richer experience for a "victim" such as myself. For two reasons, I'd posit: one, men are disquieted by a clearly feminized male. Saying anything other than "that's rough" opens them up to a host of feelings, questions, and breaches of fragile manly-man etiquette. They can't notice or pursue too many details, otherwise they'd be "checking me out", they can't ask how it feels because "they'd be wanting to try it too" and so on. So you get the bare minimum.

Secondly, women notice the little touches. A guy might not realize the discomfort in a bra or shoes. A woman will. Not to mention the implicit schadenfreude.

I'll admit to a real level of cowardice in all this. I don't go into bars, adult bookstores, or the like. I want small, safe doses of humiliation, barely worth it for some. I don't even go into fast-food joints (though I may soon) for the same reason—other customers would have little social restraint from being obscene or threatening to me. Granted, I'm a big guy, but again some men feel a need to prove their manhood through silly methods. However, at the end of the day an employee is still instinctively restricted to the employee-customer relationship, and implicit in that is a line not to be crossed.

That night, I felt like moving that line a bit...so in a way I had to give the employees permission. So I drove away, and called the pizza joint. This is our conversation:

Her: "Hello, [Pizza Place] how can I help you?"

Me (in my most gravelly voice, achieved through five solid minutes of dry hacking): "Could you tell me how late you're open tonight?"

Her: "We're open till midnight."

Me: "Could you actually do us a favor. A friend of ours will be coming by in a few minutes. He's dressed kind of funny because he lost a bet (My usual excuse). Could you really bust his ass when he shows up?"

Her: (Laughing hesitatingly): "Um, sure I guess."

She seemed unsure. Would she call her manager, or the cops? Regardless, at this point I was excited. It was a clean excitement, as before Christmas or one's birthday when you're pretty sure something good will happen. I'd never had anything bad happen to me doing this, and if that streak ever breaks, not sure how I'll move on. It was unlike the feelings I'd previously had, comparable to the excitement before a big playoff game when you know something big is going to happen, but you're far from sure you'll enjoy it.

I came back to the pizza place, whose street-side parking was empty save for a delivery car, and an employee hanging out at the front door. She didn't move for five minutes. Then ten minutes. In retrospect, she may have been waiting for me. Maybe she was staring at my car. All I know is, as soon as I got out of the car, she high-tailed it inside.

 

Section Two: Fabulous Me

 

I should probably describe, in my horribly detailed style, my appearance for the night. Now, I've long accepted I enjoy the humiliation of my predicaments. If I could pass, I'm not sure I would in most situations. And I really can't pass. Firstly, because I'm not in a place where I can shave (which the girls recognized). And someone of my large rugby-playing, "hey you can reach/move this" frame is anything but dainty..

Secondly, my 'femme persona' remains a little younger than the real me. Okay, a lot younger (and getting more so constantly). "Ashlee" is a young teenager, 14ish - flirty, silly, gossipy. A boy-crazy and trendy cheerleader if you will. But probably not a hefty guy whose hair count is diminishing far more rapidly than his weight. I might be able to pull off a "soccer mom" with dim light and great effort, but not a soccer girl. But that's what this past of me is – a sweet, fashionable teenage girl.

But hey. I am what I am (and at least being as big as I am means that

people think twice before questioning that). As typical I wore only "age-appropriate" gear – every stitch of thread dictated by teen fashions. Modern fashions, not the lace and ruffles from the 1950s. I like to detail my outfits, so if you worry your eyes will glaze, skip down to part III.

I had some white bikini panties on, graffiti'd with little sayings such as "hearts are cool" "I love stars" and "boys are awesome". I had a sparkly deep pink bra that had been a struggle to hook. Inside were two water balloons that filled up the C cups. Down below, I had black tights under a denim miniskirt with the hem ripped out. A pink sequined sash was loosely tied through the belt loops. It is an acutely feminine feeling to be constantly ensuring a skirt covers all it should, while not letting too much stomach hang out. On my feet were pink wedge heels that showed off my hot pink painted toes under their glittery thongs.

Up top I had on a pale pink shirt, made of fabric thin enough that in the right light the sparkle of my bra showed through. In darker pink, the front of the shirt was largely covered with the message "Like, totally awesome!!!" in dark pink block letters. Over that top was an open, cropped denim vest, of the same color as my skirt. The vest is the ultimate useless feminine garbage, doing nothing but being uncomfortable, getting in the way, and emphasizing my chest.

I'd hung around my neck a pendant with a low-hanging plastic pink heart. Around one wrist was a pink SuperGirl watch, around the other some pink beads. No headgear today, as my hair was long enough to be put in two tiny but notable pigtails (curling so slightly). My usual makeup was applied: smoky black eyeliner, pale blue sparkling eye shadow, and pale pink lipstick. I was hosed down in sickeningly sweet "cotton candy" scented perfume. I put the keys in my "punk princess" purse filled with makeup and my pink furry purse. My money was in the wallet, making it necessary to pay by putting the purse on the counter, unzipping it, locating the wallet, etc. Something that would be noticed.

Finally, I took off my glasses, leaving me more helpless and dependent on others (I can see well, but am not "legally allowed to drive without them"), and inside I went...

Part III: The Gambit Pays Off

I always feel an invisible force field at the doorstep. Before that, I'm still in my own world, and can back out. Once inside a store, or restaurant, or what have you, I am in another world, the domain of the employee. In this case, three laughing employees.

Attired in the corporate uniform and apron, I was delighted to see three women—two high school or college-aged, one slightly older. Perfect. No confused males to tiptoe around, just three women seeing someone from the other side utterly humbled.

And they were delighted to see me. There was no hesitation or confusion, just sheer pleasure at my expense, but of a good-natured variety. With the permission from the phone call, the ladies wasted no time giving me what for. If you read my other accounts, you'll see how rare this is. Better still, the three of them managed to rotate, firing questions between the smirking and giggling.

Some of the question I remember included "What does that shirt say? 'Like, totally awesome?' Aw, that shirt looks so perfect on you." "Do you dress like this often? (I mumbled a not-so-sarcastic "oh yeah, all the time." I mumbled a lot, more on that later).

Unsurprisingly, the breasts were an enormous curiosity. "Are those real? Where did you get those?" And the underwear: "You're not wearing a thong, are you?" (I responded truthfully that I wasn't.) When I expressed relief that I hadn't had to shave my legs, one of them pointedly noticed that I hadn't shaved my chest either. They'd clearly taken in pretty much every element of my outfit.

One girl asked if she could take a photo. I was so surprised I said yes. And she was so surprised that I said yes, she didn't know what to do. Eventually, she told me it would wind up on the Internet, so I demurred. She did venture that plenty of other photos of me in this outfit have been taken, though. I think we were both relieved about that.

While ringing up the purchase, one girl asked my name (I hesitated, giving a false male one) and town (another lie). I was told that I'd fit in better in the "weird" local town where everyone marries their relatives. When I put the purse on the counter to pay, they fawned over it: "He has a purse! Where'd you get it? It's co cute!" I replied I didn't "get it", it was someone else's, including the stupid wallet.

By the end, I was truly at ease and sorry to go. I didn't feel I could show my enjoyment too much, but I was having a good time and wonder if there was a way I could have prolonged it. I should have ordered something more complicated and time-consuming to make (I just got a salad). But suddenly ordering a pizza on a whim and hanging out didn't seem "in-character". On the way out, I was asked to drop the belt off "when I was done with it", and away I went with my food.

 

Part IV: Wherein I Get Greedy

What a thrill – what a clean and powerful thrill. Alternating between and combining obscenities and invocations of a higher power, I loudly reflected to myself on what a rush it was. I genuinely enjoyed the experience, an enjoyment that should provide ample fodder for self-analysis for weeks to come.

But a corner of me had regrets. I mean, this was an ideal situation—three enthusiastic women belittling my feminized appearance in a friendly, relaxed way. Could I have gotten more from it?

Well, balanced between cowardice and rashness, I decided to find out. I called the joint again, back in my "friend-of-the-victim voice":

Me: "It's me again. So-and-so told me he didn't get a receipt for the food, so I was calling just to make sure he actually went. We were thinking of making him come back for the receipt."

I was hoping for some excitement at that prospect, to have a reunion of sorts. But alas...

Her: "Oh yes, he was here. He looked fabulous in his jean skirt. But he said he got a boob job, though. He really liked them."

Me: "Oh, maybe we'll have to glue them on. Thanks again."

So it was a great review, but I always want more. Anyway, perhaps this was for the best. I did come away with a real thrilling memory, and a few ideas for the next time:

1 – A set-up call is a good idea. It cuts down on shock and makes everyone more at ease with the situation.

2 – It's a more vibrant experience with women.

3- I need to prepare for more enthusiasm.

 

I'd love to find a way to work it in that I am to be acting like a girl during these visits, or else, but giving extended instructions really seems to threaten believability. Oddly enough, they never asked the reason or the matter that was at stake.

Suffice it to say that my confidence continues to grow. I'll keep thinking on what I have learned, and what I can set up next time as I ease into this type of activity.

 

 

Postscript: I'd appreciate your reaction. Am I pushing the envelope? I feel bad manipulating these people, for a raw rush on my account. That said, they seemed to enjoy the experience a great deal. Part of me always wonders: are they on to me? Are they just playing along? Why?

My concern is always that I'll end up with a cashier who just moved to New England from rural Utah, see something s/he doesn't get, panic, and call the cops. Some gung-ho rookie cop will rush in and find a bullshit crime to charge me with, and this stuff will spill all over the place and ruin my life. I'm curious as to your reactions.

I'm also considering wrapping the sash as a present, and going back up there to give it (as my male self of course). Adding a note about thanks for being a good sport...and maybe an addendum that I might be back if I lose the next bet?

Admittedly, A gg or t* partner in crime could probably get more out of me seeing that I am generally a submissive, but that's not where my life is. I'd love to hear from you here or by e-mail. I'm good at replying, and can be reached at totalgirliegirl at lycos dot com

Thanks for reading!

  

  

  

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