Friday Night All to Myself

Christie was out of town again this weekend, so had no real plans. The day had been sunny, but chilly. Saturday and Sunday promised warmer weather, but tonight would be on the cool side. I expected that I’d just stay in.

I finished up what work I had and cleaned up my home “office.” I hadn’t gone in to work all week – neither at Helen’s office or my regular job working for Lauren. Both of them had given me plenty of things to do, all of which could be done at home. It was early afternoon, and I had a few errands to run. I needed to go to the office supply store and pick up some paper and report covers, and I wanted to stop by the home improvement store and get some cool-weather plants for my tiny vegetable and herb garden (another pandemic project).

I had been working in comfortable clothes – a maroon bra and panty set, an almost sheer gray yoga t-shirt, and black leggings. I thought they would be fine for a quick trip, so I just added some blue and gray running shoes. I’d be wearing a mask, so I put on some makeup around my eyes and put my hair into a ponytail.

The trip to the office supply store was uneventful. I filled my cart with the things I needed, presented a coupon for a discount to the cashier, paid and left. I drove the few blocks to the home improvement store. The store itself seemed uncrowded when I arrived. I browsed the plants, picked up a few other items, and got in line behind a couple at the only open checkout. The couple was having some difficulty with their transaction. The cashier seemed frustrated, calling a manager to help. I was in no hurry, so just gazed at the display of random things in the checkout line, not really paying attention. A line formed behind me. The cashier suddenly appeared next to me, startling me.

“Ma’am,” she said, then paused. “Oh, you have a discount item.” She pointed to a discounted, opened bag of potting soil in my cart. “I was going to have you go to self checkout, but you can’t, with that.” She directed me to a cashier in the garden section with no line.

The garden center cashier smiled at me as I approached. “That’s a cute top,” she commented. I thanked her. She chatted while she rang in my items. “Did you have the day off?”

“I didn’t, but I did get to work from home today,” I replied. I paid her, and she offered to help me take the plants and soil to my car, as a colleague had come to replace her. I thanked her again, and we walked out to my car. She continued chatting about the weather, the plants I had bought, and how cute I looked. We loaded my car and she just as quickly went back to the store. “That was kind of strange, but really fun,” I thought to myself.

I got home and put my purchases away. I hadn’t planned on going out, but my encounter with the cashier made me feel like I needed some more interaction with someone. I decided I’d go to a local winery tasting room. I’d been there before, and it had a large outdoor patio as well as some indoor tables. They were open late tonight, until 11 pm. I had plenty of time.

I felt kind daring. A few weeks earlier, Christie and I had been out together, and saw a woman wearing over-the-knee boots with a minidress. I had remarked on what a great look it was, and a few days later, Christie surprised me with a pair of black suede boots that went just above my knee. I had not worn them yet.

So I showered and washed my hair, carefully shaving my body. I twisted my hair into tight curls so that it would be wavy after it dried. I did my makeup, focusing on my eyes, but also doing my cheeks and lips, since the mask would come off at some point. I did my nails in a color that matched my lip gloss.

I was feeling excited and nervous. The winery was pretty close to where I lived. It was entirely possible that I’d run into someone I knew. I’d heard enough neighbors talk about going there and enjoying the patio. I began to wonder if my outfit might be too much. Deep down, though, I really wanted to wear those boots.

I put on a black thong and bra, nude pantyhose and slipped a black minidress on. I stepped into the boots and immediately felt a rush of excitement. They left just enough skin peeking between my dress and the top of the boots. I pulled on a long sweater to complete my look.

I walked out to my car feeling really confident. I drove the short bit to the tasting room, and found a spot right alongside the building. I stepped out and walked toward the front door. There were a few small groups of people seated outside as I walked past, but none seemed to pay me any attention.

I walked in to the winery, and a server greeted me. “Do you guys have reservation,” she asked. “Guys?” I thought to myself. I looked around and there was a couple right behind me. She must have thought we were together. I explained that it was just me, and that I did not have a reservation. “No problem!” she chirped, and showed me to a table for two right next to the open door to the large patio. It had a “Reserved” sign on it, which she quickly whisked away. She returned with a wine menu, and a carafe of water. I ordered a glass of one of their house wines, which she brought back in a few minutes. I had a good view of the patio, as well as the bar, where my server was working. I sipped my wine, and “people watched.”

I was really enjoying myself. I felt confident. I liked the wine. The number and proximity of people was well within my comfort zone. I ordered another glass of wine. As the night wore on, the place got a bit busier. One server went on break, and my server was really hustling. As she walked by toward another table, I smiled at her, and she smiled back. She stopped by my table on her way back to the bar, and asked me if I wanted another glass.

“I would, please,” I replied. “You are just going 100 miles an hour,” I added.

“Oh my gosh, thanks,” she said.

“I feel like I ought to be helping!” I told her.

“Oh, no, sweetie,” she said. “you just relax and enjoy your wine. That’s what I’ll be doing when I’m done.” She came back with my wine and squatted down beside my table. “You get the stylish points tonight.”

“Thank you,” I replied.

“You are definitely the most stylish person in here tonight. You look great,” she told me.

I thanked her again. I finished my wine, paid my tab, and headed home, feeling pretty good about myself.


4 thoughts on “Friday Night All to Myself

    1. Like my friend Kandi, I love your stories.

      I would love to hear an update of how your working while presenting as a woman has been.

      I look forward to seeing your posts.


  1. A lovely story and I appreciate how you must have felt. What’s the point in getting all dolled up and just staying at home. Public interaction is so important for me like many girls I guess and something I have missed with pandemic restrictions.


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