I Can Wear A Skirt To Work - Chapter 4

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The next morning, I was back on the job with my normal appearance. The day started well enough, but, from the first time that Jean came by for the paperwork, things started going awry.

She hadn’t been the least bit subtle in telling me that I didn’t belong there. She insisted that I couldn’t hope to fill the shoes of the person whose job I was pitifully trying to do. Her criticism actually unnerved me. I began misrouting calls, misfiling call slips, and making mistakes on the report sheets.

When the foul-ups came to Elaine’s attention, she had Diane help straighten out as many as could be found. She wasn’t happy.

"What is wrong?" she asked. "It’s almost as though you’d forgotten how to do the job. You were doing a far better job yesterday, even with your ‘handicap’."

Not wanting to be seen as trying to put the blame on someone else, I didn’t mention Jean’s influence. I rationalized to her that I’d been rattled by the rapid pace at which calls had come in earlier in the morning.

Diane tried to lighten up the mood with some humor, "Perhaps you should have taken the double-or-nothing offer, after all, Ted. Maybe the job is EASIER to do in skirts."

"Oh, sure," I mockingly agreed, "without the high heels slowing me down, I go too fast and make mistakes."

"Only one way to find out," she responded.

"Spare me."

Nevertheless, I did slow down and concentrated on being more methodical about each task, as if I were learning the job anew. Another thing that seemed to help was forcing myself to make my motions more fluid as might a dancer.

At lunchtime, Diane chose the second shift. That put me on the same lunch break as Jean and Anita.

Much as I’d have preferred to decline their invitation to join them, I couldn’t bring myself to be rude. So, along with Gregg, and Kate, I accompanied them to a nearby restaurant.

I fully expected Jean to use the opportunity to continue harping on my shortcomings. Instead, she was about as pleasant as I could ever remember; avoiding all mention of the previous day, or the way I was handling today’s work.

When we’d finished eating, everyone but Jean and I went their own way to do errands. That was when she finally started laying it on.

"Well, you couldn’t cut it, after all, could you?"

"What?" I asked mechanically before her meaning had registered.

"You know, in skirts and heels. You couldn’t do a simple job that any woman could do."

"That’s baloney, and you know it. I was doing the job; I lost on a technicality. Furthermore, I’d bet that any woman would have trouble with the heels, too, if she hadn’t ever worn them before then."

"Are You complaining that You didn’t get enough practice?"

"Forget it."

"Oh sure, now that you’ve failed, you want to hush it up. Well, the next time you think you’re as good as a woman, just remember yesterday."

There was no reasoning with her, so I was silent the rest of the way to the office.

A little later, Diane was commenting on the graceful way I was navigating around the dispatch station, and I let it "slip" that I might be interested, after all, in trying for the double-or-nothing.

"I don’t know if that offer is still open, Ted," Diane remarked. "I’ll ask around."

Jean made a show of objecting to a repeat of the offer, but let herself be persuaded, perhaps with uncharacteristic ease. Kate proved to still be amenable to the deal, so I found myself being invited to Diane’s place after work.

"This time, we draw up a contract, spelling out exactly what is expected," she advised me.

Alarms went off in my mind.

"What do you mean ... a contract?" I exclaimed.

"Just that, if the expectations are in writing, there won’t be any ambiguities to be disputed after-the-fact."

Elaine, having heard part of the exchange, came out to the dispatch center.

"What is going on?" she demanded.

Diane explained.

After a moment’s silence, she sighed.

"I do hope you haven’t forgotten that this is a business, not a playground for your ‘inner children’," she reminded us.

I felt a sudden inclination to drop the whole matter.

She turned to me, however, and asked, "Why are you putting up with this?"

Now on the defensive, I found myself trying to justify the situation without any real conviction behind my logic, "It seemed like an easy way to get a couple of week’s worth of dinners."

Her stern expression melted slightly, into an exasperated grin, and she shook her head. Turning her attention back to Diane, she said, "Goddess help me, I hope I don’t end up having to justify to Region why I’m allowing this nonsense."

An hour after work, I was in Diane’s living room, negotiating the terms of my "contract".

When all the details had been worked out and committed to paper, the group dispersed. Jean offered to stay and help Diane prepare dinner.

Diane suggested that it would be to my advantage to get all the practice on heels I could, before work tomorrow, so why not start right now? That turned out to mean: with pantyhose and a skirt - the same one I’d worn yesterday.

After dinner, Jean suggested, half in jest, that we go to a movie. I was willing - as soon as I could change into my own clothing. I should have known better.

Jean was interested only if I went as I was. That discussion was aborted when Kate rang the bell, and Diane let her in. The discussion turned back to the coming day, and how I simply COULDN’T wear the same skirt twice in one week.

When I asked ‘why not’, Kate observed that it was a feminine custom. "Also," she pointed out, "you spilled some of your desserts on it."

Consequently, I have presented a different skirt, white, with a linen texture and box pleats.

Then they invited themselves over to my place to find an appropriate shirt to go with it.

Kate had brought in another pair of pumps, with low, two-inch heels. When she offered them for me to wear during the trip, my objections were sidetracked by Jean’s protest.

"I hope those aren’t the shoes he’s wearing for work," she said.

"I thought they’d do for the spare pair," Kate explained.

"Spares would have to be the same height as the first pair," Jean stated flatly.

Kate looked over to Diane, who didn’t object.

"OK," Kate agreed, "but these will do for the trip to Ted’s place."

I didn’t really want to go outside again, dressed as a woman from the waist down, but after Kate had taken my side, I didn’t have the heart to argue the issue with her. So, still wearing the plaid skirt and the mid-heeled shoes, I was escorted out to the parking lot, where we all got into Kate’s car.

I live in a rambling old cottage, twice extended by previous owners. It sits well back on a deep lot, shaded by a thick canopy of old trees. Because the view of passersby was blocked by heavy shrubbery, I wasn’t bothered about going from the car to the house, dressed as I was.

Inside, matters soon became a little more complicated. Although they found a dark blue oxford shirt that looked OK with the skirt they’d brought, none of the women thought it a truly suitable pairing.

Kate went out to her car and brought in a top that obviously was the mate to the skirt. It had three-quarter sleeves, a jewel neck, and buttoned up the back. It wasn’t near as much trouble as they might have expected to get me to try it on. However, after I saw myself in a mirror, I didn’t like the mixed image.

Jean started teasing me about how I was starting to look quite cute, and that a little makeup might help even more.

After that comment, I prevailed upon Diane to unbutton the top, and I went to my room to change into a jogging suit.

When I returned, Diane reminded me that I’d have to go back to her apartment for my car. Then she extended an invitation for me to spend the night in her apartment. Her housemate had two weeks to go on an overseas assignment, she explained. She was sure that Carol wouldn’t mind if I used her room.

"That way," she rationalized for me, "you won’t have to get up so early, yet you’ll have plenty of time to get ready for work."

I couldn’t think of any rebuttal to her logic - or even to ask why I’d need much time to get ready. Taking my lack of objection as capitulation, they helped me gather up the items I’d need for that night and the next day.

Back at Diane’s apartment, Kate brought up a large case, as well as an overnighter. Among the items inside were two pairs of dress pumps that had the same heel heights. That was how they got me out of the jogging suit again, by insisting that I had to try on the whole outfit for tomorrow, including both pairs of shoes.

When I got to see myself in a full-length mirror, I again became dismayed at the mixed image. Somehow, the contrast hadn’t been so strong with the plaid skirt.

That seemed to be Kate’s cue. She turned on the charm, asking me to please go along with them for just a few minutes - which turned out to be two hours - and let them try a different approach.

Soon, I was back in the linen suit, wearing pantyhose which bore a faint honeycomb pattern and ankle strap pumps.

That put me at the precipice of my comfort zone. What they wanted next, pushed me right over the edge.

"It’s so close," Diane mused.

"Why don’t we see it?" Jean asked cryptically.

Diane led me into her bedroom.

"Sit down right here," Diane directed, pointing to a padded stool next to a small table.

Tilting up the top of the vanity to expose a mirror and a compartment underneath, she removed a bottle. She soaked a square cotton pad with a portion of its contents.

When she began wiping it across my face, I reached up and grasped her wrist.

"What are you doing?" I demanded.

"Just cleansing your skin," she answered. It was in a tone of voice so absent of guile, that I let her continue. "How often do you shave?" she asked, as she gently stroked my face.

"A couple of times a week, I guess," I responded.

"That’s unusual for a twenty-five-year-old, isn’t it?"

"Not in my family," I said. "My dad didn’t need to shave every day until he was nearly forty, neither did any of his brothers.

When she had finished, she brought out another bottle, which I immediately recognized. It was liquid makeup.

"Whoa, there. You aren’t thinking what I think you’re thinking, are you? You’re not putting any of that stuff on me - no way."

Then the air was filled with the sweetest pleas and "please’s" for my indulgence. Wouldn’t I just let them show me what was possible? It would wash right off, afterward ...

Their appeal to my male nature was so transparent, that it was disarming. I had it in my power to make them happy, merely by sitting there - and letting them have their way with me. Well, it wasn’t exactly in a way I might have wished for. Still, all that attention was intoxicating, so I acceded.

By the time they had finished, I was sure I knew how an artist’s canvas might feel. After the liquid foundation had been spread, blended, and set with translucent powder, they began applying other powders in various hues. Kate stroked each side of my nose, and the tip of my chin, with a brush bearing traces of tan.

Diane made me smile, then lightly dusted the fullest part of my cheeks with pink, and followed with a darker shade just below. Next, she took a clean brush and went over the same areas, with an interruption to use a previous brush to add a little more color to one side.

Kate took over, and with light and dark shades of a brick-colored powder, began dusting my eyelids. Next, she used a dark pencil to draw along the edges of my eyelids. She followed with a cotton swab in short strokes that didn’t feel like they quite followed the way she’d drawn the original lines.

When they were both satisfied, Diane fitted me with a wig. It was a dark, golden blonde in color, and not quite shoulder length. She arranged it with an odd sort of comb which had only four, long, widely spaced, teeth and rattail handle.

Only then was I allowed to see a mirror. I found myself unable to deny that they had done an excellent job. I wasn’t exactly pretty, but my own mother probably wouldn’t have recognized me, or even - perhaps - that I wasn’t a woman.

Still, the suit didn’t look quite right; I wasn’t curved in the right places. Returning to the case, Kate removed a long-line brassiere and some pads for the cups; then she retrieved a panty girdle that had pads strategically placed.

They moved me along quickly, forestalling any questions: suit off; foundation garments on; a full slip, much fancier than the half slip I’d used at first - a little lace would show in the walking slit; then back on with the suit. Much better. Clip-on some earrings. Another look in the mirror.

"This is unbelievable," I whispered.

Kate gently suggested that I was so convincing that no one could possibly guess that I wasn’t what I appeared to be. Furthermore, she insisted, this person before them was far too feminine to be even a "Teddie", much less a "Ted". Her conclusion, therefore, was that they ought to call me "Tess".

Had the same thoughts been expressed by Jean, even in the same tone of voice, I would have taken instant offense. Instead, I was so much under the spell of the moment that it entirely escaped me that a guy shouldn’t think of that as much of a compliment.

Jean decided she’d had enough for tonight.

"I’ve got to get some sleep. See you in the morning."

A round of hugs, and Jean was gone. Then Diane began to ply the "big sister" routine in earnest.

"Ted, you might want to consider going into the office like this, instead of just half-and-half."

My eyes went wide. "Why?" I said.

Kate took over "For one thing, because you’ll be less likely to get unwelcome attention from outsiders."

"Which is bound to make Elaine feel better about this," Diane interjected.

Kate continued, "For another, I think you’ll have an easier time with the in-house people, too. That gender-bent image you presented Wednesday will just get you a lot of unwanted attention."

"And you think that showing up, completely made over as a woman won’t?" I asked incredulously. "Anyway, that’s not the question I meant to ask. Let me try again. Why is it that YOU want me to do this?"

"Because you are a macho pig," Kate teased, adding, in a dramatic voice, "and we want you to walk a few miles in our ‘high heeled moccasins’ so you can know what it’s like for the other side."

As if on cue, Diane continued Kate’s thought, with equal exaggeration, "It’s the least you can do, you know, considering the thousands of years of oppression we’ve suffered at the hands of you men."

After working with me for two years, they knew how responsive I was to wry humor.

In a sudden reversion to seriousness, Kate moved in to close the sale.

"Because we want you to win."

I tried to counter, "I can win without all this other stuff," gesturing at my head and upper body. I saw a satisfied smile form on Diane’s face, which she quickly suppressed. Instantly, I realized it was because the gesture had been executed in a feminine manner.

Weakly, I tried again, "Why aren’t you on Jean’s side? You’re each committed to equal shares of the dinners. If I win, you lose."

"I only did that to make sure Jean got her hook set firmly in her own gills," Diane answered.

That left me speechless.

She continued, "Honestly! It isn’t as if you’d never been invited here for dinner, before this."

With Diane pushing my ego with the prospect of forcing Jean into providing dinners for me, and Kate assuring me that I appeared absolutely authentic, my resistance was crumbling. Add an "assist" from the image I saw in the mirror, and my defenses were overwhelmed.

Once I had committed myself to that, it wasn’t much more trouble for them to finagle me into going with them, as I was, to get frozen yogurt cones at a nearby Dari-Delite. All they had to do was assure me that we’d go through the drive-through, so I wouldn’t have to get out of the car.

I became apprehensive when Kate insisted I sit upfront. She chose to sit behind Diane. However, once we were there, I realized she’d done me a favor, by putting me as much out of view from the service window as was possible.

I wasn’t sure if Diane was teasing or not, when she suggested that we take a parking place and eat right there. Fortunately, she yielded easily to my pleading and drove directly back to her place.

All the excitement - and the extra time it took to remove the makeup - rendered me one tired soul when I finally collapsed into my borrowed bed.