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I Can Wear A Skirt To Work - Chapter 6
🕑 Added 2025-04-04 14:16:09 +0000 UTCOTHER CHAPTERS | ALL STORY LIST
I awakened in surprise at the brightness of the daylight streaming through my window. I had slept soundly, clear into midmorning. I closed my eyes again, and waited, listening to the sounds coming from outside. This was supposed to be a laid-back day for me. I hadn’t scheduled anything for the whole day. I turned over, away from the light, before I tried opening my eyelids again.
My expectations of a carefree day were shattered by the sight of the clothing draped over the drawer. It would be rude to return dirty clothing to the people who’d lent me the various items of yesterday’s outfit, and the suit probably had to be dry-cleaned.
That was just the beginning. Jean would be expecting me over for dinner, and ...
"Oh, heavens!" I thought aloud. I hadn’t told Diane or Kate about Elaine’s request. What if they can’t - or won’t - help me?
I was overwhelmed with a feeling of doom. What if they did help me? The whole idea of working as "Tess" for an entire week was utterly crazy. It would get back to regional management, and then Elaine and I would both be fired. Wouldn’t that look great on my next job application: "fired because I came to work dressed as a woman." I didn’t dare ask for help, but, after my promise to Elaine, I didn’t dare ask, either.
I threw off the covers and stomped into the bathroom, in the hope that I’d think more clearly after a shower.
After I dried off, I had to move yesterday’s clothing to get at some fresh underwear. The sensation of the slip-sliding across my forearm raised goosebumps. As I placed the pile on my bed, I regarded the underclothing I’d been wearing several hours earlier. I had enjoyed the silky envelopment of the panties around my loins. I didn’t miss the bra, with its band cinching my torso, and straps digging into my shoulders, nor the girdle - although a pleasant side effect of wearing it had been not getting anything pinched whenever I sat down. The slip, on the other hand, had provided a delightful tickle on my legs whenever I was moving around.
I picked the panties up, enjoying again the silky feeling of the material in my hands. Suddenly, I wished that they were clean. With a sigh, I dropped them back onto the pile and turned to my chest of drawers for my own clothing.
Still struggling with what I’d do about next week, I put off calling anyone until after breakfast - or rather, brunch.
It was eleven-thirty. If I waited too long, Kate might not be home.
My phone rang.
I wasn’t even thinking about how I answered it.
"Good morning," I heard Kate’s cheerful greeting. "Is this Ted or Tess?"
My voice dropped a full octave.
"Very funny, Kate," I replied, drolly.
"Ah, it IS Ted," she said.
"Look, as long as you called," I opened, "I need to ask a favor."
"Yes, I know," she told me. "Elaine called me this morning, to ask if I would help you."
"I take it that she didn’t have much confidence that I’d follow through."
"Not at all. It was more like she feared you wouldn’t get any cooperation."
"Jean called, too," Kate added, "to ask if I could handle the dinner arrangements tonight. She has to go down to her folks’ this afternoon. It seems everyone wants my favors today."
I ignored the double entente, "Maybe I should call in sick next week."
"Why?" she exclaimed. "We can get you set up with whatever you’ll need."
"Kate! This isn’t going to work. Sooner or later, someone is going to figure me out, or someone in the office will blow my cover."
"No one did last night," Kate reminded me. "And Elaine was already asking around the office, yesterday, to see if everyone would keep their mouths shut about you."
It took a little more talking, but she eventually had me marginally convinced that I’d be all right next week. Then she invited me to her place for dinner at 4:00 PM.
I accepted - remarking that I’d had breakfast late, so why not an early dinner.
She replied that dinner wouldn’t be ready until 8:00. Better still, she suggested, how soon could I come over? We’d make a day of it.
Of what? Getting me ready for next week, of course.
I told her I’d have to take yesterday’s suit to the dry-cleaner’s first.
Kate advised that it was washable, in cool water, using the delicate cycle. Then she asked if I could come over right away.
I couldn’t think of any reason not to, so I said yes. In a few minutes, I was on my way. I had no way of knowing that it would be nearly midnight before I returned.
As soon as I arrived at her place, she sent me down the hall to her bathroom, insisting that I wear a pair of ladies’ white nylon briefs and camisole under my clothes, instead of my own underwear. Despite my feelings that morning, I was resistant. I didn’t want her to know that I liked the feel of the silky underwear. She told me to wait there, then went into her bedroom and brought out a pair of pantyhose.
"These too," she ordered.
I didn’t move fast enough to suit her.
"Better hurry, before I get more adventuresome," she warned with a mischievous giggle.
Shaking my head in bewilderment, I did her bidding.
"Come on - time’s wasting," she urged when I came out.
"Where are we going?"
"Lots of places," she said. "We have to get groceries for dinner, arrange for you to have clothes to wear to work, and get you set up with your own makeup."
"Makeup?"
"You can’t expect to borrow someone else’s for a whole week."
That made sense, but I bemoaned spending the money.
"Look," she explained, "If you want to do it right, it’s going to take a little money. Think of it as an investment - Elaine told me what she’d promised you for this gig."
"She didn’t promise me the promotion - only her help."
Incredulously, she asked, "You think if she signs the request, it isn’t a lock?"
"IF she signs," I reminded her.
"Ted, paranoia is clouding your mind. Of all the people I’ve ever known, Elaine has been the most, reliable, at honoring her word. She says it, she DOES it. You should know that as well as I do, by now."
I mentioned that she deserved promotion as much as I did and that helping me with this could actually be giving me an unfair advantage over her.
Kate’s response was that she was my friend, and she was happy to help me. It would be bad karma for her own prospects if she didn’t help when she could. She said it so kindly, I couldn’t argue.
Once we were out doing the errands, I was glad I’d worn a sweatshirt. The sensation of the camisole fabric rubbing against my nipples kept them taut. Moreover, something thinner - like a T-shirt - would have let the lace trim show through, too.
Kate led me on what was, for me, a unique tour through the regional shopping center. At first, we just went from store to store looking at the displays. She wanted to see what I thought looked good and what I didn’t like. Then we went into the largest department store there, straight to the lingerie section. Again, she picked out various articles, asking my opinion. Likewise, at the shoe store.
Our last stop of this trip was for groceries. When I saw the cosmetics aisle, I asked if we were getting mine there. She said no, explaining that it would be almost impossible to get the right shades on the first try. We’d be going to a specialty shop instead, where I could get a custom match.
"Won’t that be expensive?"
"Not as expensive as getting the wrong shades and having to buy more."
First, we went back to her place, to put the groceries away. Then, saying that she had some private errands to complete, she told me to enjoy a nice soak in her tub while she was gone.
"I took a shower this morning," I objected, "I can’t smell bad already."
"You smell just fine ... for a man. However, Tess will need a different air about her," Kate explained. "Besides, how long has it been since you’ve enjoyed a long, leisurely, bubble bath? Twenty years?"
I shrugged in accession.
"When you’re finished, use this bath powder all over your body. I’ll leave out a clean set of underwear for you."
I started the water running and added the bath oil.
On the sink counter, Kate deposited a pastel blue camisole and panty set, plus another pair of pantyhose.
She was away for nearly two hours.
Our last trip of the day was to a little cluster of shops away from the main part of the city. It was nearly closing time when we entered the studio.
The lady inside was pleasant and unassuming. Kate explained what I needed (the works!) and Mara brought out color swatches and charts. She then steered me over to a mirror ringed by lamps that could be adjusted to different hues. By the time we were done, it was getting dark, and my Master Card debt had grown by eighty dollars.
At first, I wasn’t going outside that shop until they let me clean everything off. However, Kate had prepared for this. She went out to her car and came back with a cylindrical box and a bag. The bag contained a bra, a set of pads for it, and a pair of high heeled sandals in navy. The box contained a wig, longer than the one I’d worn Friday, and in a lighter shade.
"Good thing I had you wear pantyhose, isn’t it?" Kate observed.
I was still resistant.
Kate must have been a champion debater in college, every time it came to something that was important to her, she got her way.
They had me walk around the shop for a few minutes to get used to the wobbly nature of sandals with high heels. Then Kate and I were let out of the shop, so Mara could close up.
When we got back to her place, Kate insisted that I take off the sweatshirt and jeans and wear something more appropriate. She went to her room and brought out a sleeveless sun shift, which buttoned up the back. Handing it to me, she turned me toward the bathroom.
"Hurry up. I’m going to need your help preparing dinner."
It took some doing, removing the wig without mussing it, so I could get the sweatshirt off. I also had trouble reaching the buttons at my back to fasten the dress.
After the wig was back in place, I folded up my clothes, and carried them out with me. Still in the hallway, I called, "What’ll I do with my clothes?"
Kate called back, "I hope you’re wearing them."
I reached the kitchen door.
"You told me to put on this dress."
"That’s right," she said, as she took the bundle from my hands. She walked back into her bedroom.
When she returned, she reached behind the pantry door.
"Here’s an apron to protect your dress."
I put it on, and began helping her get dinner ready.
"I had no idea, when I accepted the bet," I chuckled, "that I’d still have to prepare the dinners I’d won."
"You don’t have to help, Tess," she said, "if you don’t mind waiting until midnight to eat."
I tried not to show that I’d noticed her switch to the feminine appellation.
"I’ll help, already. I haven’t eaten since this morning."
"That’s how we girls keep our trim figures," she said, as she gave my waist a quick hug.
The rest of the evening - through the meal, and the cleanup afterward - she made a running critique of my actions, voice quality, and vocabulary. It seemed that nearly everything she said to me involved some variant of, "A woman doesn’t ... " or "This is the way a woman ..."
Once again, I drove home dressed as a woman. Now I had two feminine outfits that needed to be cleaned and returned - or so I thought. It would be well into the next day before I would begin to realize that I was being carefully conditioned to ENJOY functioning in a feminine mode.
Comments
Amanda
A very warm and encouraging environment. Loving this story❤️😂
