Retail Therapy

Last week, Lauren suggested we do some clothes shoping. She had a business trip coming up, and needed a few things. She thought it would be fun if I came along. I could update a few things in my closet, too.

We decided to go on a weekday, avoid the crowds at the mall, and take a break from work. It was a warm day, so I decided to wear something comfortable.

I had a skirt that I always wanted to wear but never did, and this would be the perfect opportunity. It is a green paisly design that was about mid-calf length. I generally go for something shorter, but I liked this style. It had not one, but two fairly high side slits, and revealed a lot of leg when I walked. You can’t actually see it in this picture, but there’s a second slit on the right side of this skirt.

I did my nails (and my toes!) with a teal colored nail varnish. I really like the color, and it matched the skirt pretty well.

Lauren looked really cute in a short blue floral-patterned sundress. She has kind of naturally olive skin, and she really looked stunning.

We shopped at a couple of stores, and Lauren picked up the things she needed for her trip. We peeked into a couple of other stores, more window shopping than serious deal-hunting. I was beginning to think I wouldn’t find anything for myself, until we walked into a small shop that had quite a few sun dresses on display. I picked out a white floral patterned one, tried it on and fell in love with it.

This is the new dress. I put it on that afternoon, and Lauren and I went to our local wine tasting room to relax, after our day of “retail therapy.”

Walking the Walk

One of the things I learned from working from home and being cooped up at home was how important it is to get out in the fresh air and get some exercise. I was talking to Lauren about this last month, and we both resolved to do better. Lauren agreed we could both do to lose a few of the pounds the pandemic put on our respective waists, so for the past few weeks, we’ve been walking.

A few years ago, the city I live in had renovated a section of land along a river, removing some concrete banks put in as flood control, and replacing them with native plants and a curving, paved path. It wasn’t heavily used, and was between Lauren’s place and mine, so we decided that would be “our” walk. We meet at the parking area at one end, walk to the other end of the trail and back, covering just over three miles.

When we planned our first walk, Lauren let me know that she planned to wear leggings and a light, long-sleeve athletic top. I hadn’t really thought about what I would wear but agreed to wear something along the same lines. I had a pair of cute black leggings with sheer panels down the sides. A quick trip to the sporting goods store netted me a purple, strappy back sports bra and a long-sleeved tee, short-sleeved tee, and tank top.

The walk felt great, and it’s become a daily thing for me. Lauren frequently comes along, but if she can’t make it, I still go. It has really helped me, both physically and mentally.

Just this morning, Lauren and I met and walked. It was cool, but I thought that once we started walking, I would warm up quickly. I decided to wear a pair of lycra shorts, a pink sports bra, and a white tee. The tee is one of those moisture-wicking athletic ones and is sheer enough for the pink bra to show through a bit. We had the trail to ourselves today, had a nice, brisk walk, and saw some really interesting birds along the trail. Lauren was feeling playful and took a picture of my behind as we walked.

Getting Back Out

I has been a long, difficult two years, and I must tell you that I have struggled. I really don’t want to dwell on the past. I do want to apologize for not writing more; it probably would have helped me get through some of what I have been dealing with. I will try and look forward, be positive and share with you what’s going on.

About a month ago, after quite a long spell of not going out, I decided I needed to get my hair done. I made an early afternoon appointment with my stylist, Allison. I had gotten comfortable with my previous stylist, but she left a few months ago.  I made an appointment with “next available stylist,” which happened to be Allison. She is very sweet and does amazing things with my hair.

It was a little cool on the day of my appointment. Since it was early afternoon, I wanted to look casual, so I chose a pair of black leggings, a black spaghetti-strap tank top, and an oversized yellow plaid shirt. I picked my white sneakers out from my closet. I kept my makeup minimal since the shampoo and rinse would make a mess of anything more. I used some BB cream and a little powder to even out my complexion, and put on some brown and pink eye shadow, along with some pink lip gloss. I put on some pink nail polish and felt happy with the result.

The salon is just a few minutes away, but parking can be limited, so I gave myself plenty of time.  Fortunately, I found a spot just behind the building. I was early, so I spent a few minutes in my car, checking messages. Ten minutes before my scheduled appointment, I walked around to the front of the salon and went in. The receptionist greeted me, offered me a cup of tea, and let me know Allison would be right out. I sat down at the table in the waiting area and enjoyed some tea.

Allison came out a few minutes later. “Gee? How are you.  It’s been a while!” she said as she smiled and motioned me toward the changing room. “Just hang your shirt up and put on a smock. I’ll be waiting for you out here.” She was as cute as I remembered.  She had on some black cropped jeans, black sneakers, and a loose black top under her apron.

She led me to a chair, then took a seat next to me as we decided what we were going to do.  I wanted to lighten up my hair a bit, going a little redder, as well as cover up some early gray around the temples.  We chatted a while, then Allison went to mix up the color.

We talked a bit while she worked, and Allison asked whether I had any plans for the weekend. I admitted that I didn’t but was starting to feel in the mood to do something fun. It was about then that I felt Allison leaning on my arm. My arm was on the armrest, and as she brushed the color onto my hair, she leaned heavily onto my arm. I’m sure it was accidental.  She’s a professional. But it was difficult to ignore an intimate part of her body pressing onto mine. I thought about and it seemed to me that hairstyling is an extremely intimate job. Still, I hadn’t noticed her do that before, and it was kind of “what do I do” moment. I was certain she didn’t mean anything by it, so I tried to ignore it.

Allison washed the color out, dried and began to style my hair. We discussed how I usually style it, and she blew my hair and flat-ironed it.  I kind of expected her to use her curling iron, but we decided that it looked pretty when it was straight. It also looked much longer. The color was perfect.

Allison finished up, stood behind me and looked at me in the mirror. We were both pleased with the results, so she had me go to the changing room, take off my smock and meet her in the waiting area. As I left the changing room, I almost stopped cold. Sitting in one of the chairs was a co-worker of mine. I guessed he was waiting for his wife. I didn’t know him well, and hadn’t seen him in a long time, but there was no mistaking him. I kept walking, and he looked up and seemed to stare at me for a short time – as if he thought he might know me but wasn’t sure from where. I saw Allison and went to her. She had set out some of the products she had used and after explaining them to me, took me to the cashier.  I remembered her from my last few appointments. She complimented me and Allison on how pretty my hair looked and commented on how long it has gotten. I paid for my service and a couple of products, and walked back out to my car, carefully avoiding meeting my co-worker’s eyes.

I left the salon and was feeling confident. I decided to run a few errands on my way home, stopping by the dry cleaner, the local BevMo and the grocery store. By the time I got home, it was about 4:30. I still didn’t have any plans, but I desperately wanted to do something. I remembered that the wine bar near my house opened at 4 pm, so I decided to go there. It was a weekday, and I didn’t expect it to be busy.

I though about what to wear.  After I freshened up my makeup, I put on a black knit minidress.  It had started to rain lightly, so I threw on a knee-length sweater and some ankle boots.  It was a cute look.

I found a place to park close by, so I didn’t have to worry about the rain too much.  I walked in and found a seat at the bar.  The bartender, Vanessa, didn’t remember me (it had been quite a long time since I’d been in). She offered me a wine list, and I selected glass of red.  It was fun to watch the few people who were there. I asked Vanessa a few questions about the wine, stayed for a few more glasses, and decided to go home before it got too late. 

Ch-ch-ch-changes

Eight months have gone by since I last wrote something for this blog. So much has happened that I should have written about. I struggled a little bit. I hesitate to say that because, honestly, many people have much more significant things to deal with in their lives; thankfully, mine are manageable. Perhaps writing about them as they happened would have helped. Maybe sharing them now will.

Pandemic life has been strange for everybody. Christie ended up working exclusively from home, which was wonderful. I inherited a closet full of work clothes, which, with a little alteration, fit me well. We made a very nice home office for her, and got into a good routine. Then, around last February, her sister on the east coast began to struggle. It looked like she was going to lose her house. It took a few weeks to decide, but in the end, Christie moved in with her. Christie’s job paid well enough to cover the expenses, and they both saved a bunch of money.

It was hard, though. Christie and I have been best friends for years. Seven years ago, her dominant side came out, to which I willingly submitted. We still keep in touch, texting and talking a lot, but I miss her. I really don’t gone out socially as much since she left, and I miss that, too.

I still work for Helen, part-time. Since tax season ended, she’s been working mostly from home, and I only go in to the office once or twice a week. Usually the office is mostly empty. Since none of my co-workers there has ever seen me as a ‘guy,” I always take the time to dress, put on makeup and do my hair. If we’re both at work at the end of the day, we tend to go out for a drink. Occasionaly, Helen will get tickets to a show and we’ll go out, along with one or two of her friends.

My relationship with Lauren is more complicated. She is my supervisor at work, and she worked really hard to get me into her division when my company closed down my section, early in the pandemic. We all work mostly from home, with lots of video conferencing and occasional meetings in the office. For whatever reason, all of the people in Lauren’s section are women. It was Lauren who encouraged me to start dressing at work. She (and all of my colleagues) really does support me being whoever I want to be gender-wise. I’m pretty sure she’s let HR know. Early on, I never considered this to be about gender. It was a thing that Christie and I did, and I suppose it’s evolved, especially now that Christie is gone, to something more. I can’t imagine not wearing makeup and womens’ clothes, to work or anywhere else, any longer. It would seem…wierd. Lauren has also encouraged me to spend some time with a counsellor, which has really helped me, honestly.

I did let some of the routine things lapse while I was working things out, and I noticed that some gray had crept in to my hair. I made an appointment at the salon I go to, and found out that Jasmine, my stylist, had left. For some reason, I was really nervous about making an appointment with someone new, but eventually I did. The day before my appointment, I started to really worry about what to wear, so I decided to do some shopping. I found a shirtdress that I liked, and got some opaque black leggings to wear with it.

The next morning, I did my makeup and nails and dressed. I arrived a little early, and had to wait a few minutes for my stylist, Mercedes, to arrive. She was wonderful. She complimented me on how “cute” I looked, and together we came up with a really nice color for my hair for the fall and winter. It’s a little deeper than before, and we decided to forego the highlights.

I’ll show you an “after” picture; there’s no need for you to witness the gray. I apologize for the shot – I am not a “selfie” person. (The picture at the top of the post also features my new shirtdress.)

Work and Play

This has been such a strange year. In March, when California issued its first “stay at home” order, I had my hours significantly cut back at work. I wasn’t sure just how I would survive until Helen, who is a CPA and friend of Christie and I, put me on her payroll for two days a week.

For the past five years or so , I would work for Helen on weekends, helping her get caught up during her busy tax season. Helen and Christie thought it was fun to have me go to work in women’s office attire. I worked for free, with nobody but Helen ever around, and I grew comfortable enough with her that wearing a dress while doing office work for her seemed pretty normal. I only occasionally had to interact with her clients in person, and that was just to bring Helen copies of paperwork or carry in refreshments or something.

This past year was different. She actually put me on payroll, and had me come to work for her during the week. At first, since it was tax season, I went to her office two days a week. Health safety rules meant that there really weren’t a lot of people around. Helen’s colleagues worked mostly from home and took turns coming into the office. I got a bunch of new clothes out of it, and once again became pretty comfortable going in to work. It felt to me, since I wasn’t around a lot of other people, that this was an extended version of what we’d been doing all along, mixing work with a little fun and excitement from Christie and Helen’s challenge. Having a source of income was nice, too, since my “real” job has been 100% work from home, and not much work at that.

This tax season, which started for Helen about a month ago, has been really busy. There had been a lot of changes, so Helen, as a CPA, was more focused on that, while I had a lot more of the routine things to do. Most of Helen’s colleagues still work from home, but they had begun leaving things for me to do as well – mostly copying, filing, mailing, and calling clients to set up appointments. I gradually began working more hours, and now I’m working four days a week.

It seems strange to me, how normal it feels. In the past, it was exciting to dress up, put on makeup and go out to a bar with Christie or Lauren, feeling anxious at being in public, with only one or two people knowing my “secret,” and eventually forgetting the anxiety an getting comfortable. Now, I get up, shower, put on makeup and dress, and go to work in an office. There’s always the anxiety at first, with only Helen knowing our “secret.” Eventually, I get comfortable and focus on work, with occasional slightly scary moments when I have to interact with people.

Friday started like most days. I got up and showered, carefully shaving my legs, arms and chest, and washing my hair. It’s been too long since I’ve had my hair colored, so I started using a color-depositing conditioner that leaves my hair a nice red tone. I did my makeup, choosing some eyeshadow that I thought worked well with my hazel eyes, brown eyeliner, and a coppery lipstick. My nails looked good, so I left them the way they were – “Wine with Everything” is the color. It’s been a little cool in the office, so I put on some pantyhose, and a black padded bra with my silicone breast enhancers. I chose a black skirt, and a sleeveless black-and-off-white zebra-striped top that Christie gave me. I put on a black blazer jacket and headed to Helen’s office.

I parked and let myself in, turned on my computer and made coffee. When Helen came in at 8:30, she was with one of the partners she works for. She introduced me, saying “Jerry, this is Gee. She’s been with me almost a year, now.”

Jerry reached out to shake hands, thought better of it, and clasped his hands over his chest, bowing slightly. “Nice to meet you, Gee. Helen tells me you’re doing a great job.” I smiled behind my mask, nodded slightly, and said “thank you, sir.” Helen and Jerry went into her office. I was nervous that the boss was there, but I knew Helen would want coffee. I put a cup on a tray. I poured a cup for Jerry, along with a bottle of water, in case he didn’t want the coffee, and took it in to Helen’s office. Jerry took the coffee cup, saying to Helen “wow, she really is a mind-reader. ” I smiled and handed Helen her cup. I went back to my desk and went to work, preparing some returns for signatures.

After a while, Jerry left. He stopped by my desk. I had about two dozen returns laid out on a table, with little “sign here” stickers at the appropriate places. He saw that I was busy and thanked me for the coffee. “Very nice to meet you, ” he added.

Helen came to my desk and smiled. “You like very nice today, Gee.” I thanked her. “I’d been telling Jerry what a great help you’ve been, and how much more you’re doing for the other accountants. So he authorized me to give you a raise!” She smiled. We were standing pretty close to each other, and I instinctively hugged her.

“Helen, I have no words…” I began to say. I was so happy. Helen suggested we finish as early as we could, then take a late lunch to celebrate. By about 1:30, we had everything put away. We got in our cars and went to a restaurant nearby that had a large outdoor patio. The hostess greeted us and led us to a table at the edge of the patio. There weren’t many other tables occupied, as lunch hour had pretty much ended. We ordered drinks.

“I can’t remember the last time we did this,” I said. “Thank you so much.”

“It’s all you, sweetie,” Helen replied. “You really do a great job, and your covering what was four different assistants’ jobs.” It was pretty warm beneath the patio heaters, so I took my jacket off. “You look really pretty, today, Gee,” she said with a smile. We ordered some light appetizers, enjoyed some drinks and talked. About an hour later, we paid our bill, hugged, and went our separate ways home.

I couldn’t wait to tell Christie, so I called her as soon as I got home. She has been working from home since this all began (she actually gave me most of her work clothes, which, with some alteration, fit pretty well). We decided she would come over that evening, spend the night, and then we would go hiking the next day. Hiking has turned out to be our new favorite outdoor activity, and there are a lot of really nice trails nearby.

Christie arrived about 7 that evening, and we ate pizza and drank wine while we talked. We ended up having a really intense discussion, followed by equally intense sex.

The next morning, we got ready for our hike. It was breezy and cool, and promised to be even cooler near the ocean, where we were heading, so both wore leggings, sports bras and tank tops, and carried light jackets. I wore a light blue tank top that fit slightly loose, so my pink sports bra was visible under my arms. I brought a small day pack with water. Christie had bought us both wide-brimmed cloth hats to keep the sun out of our eyes and off of our ears and neck; both of them were a soft pink.

It took us about thirty minutes to reach the trailhead at the Laguna Coast Wilderness Park. We had picked a loop of about four miles that ran up a ridge to some great ocean views, past a waterfall (no water this time of year, though) and through some coastal oak woodlands with amazing flowers. There were plenty of others on the trail, so we pretty much kept our masks on, but the trail wasn’t crowded. It was a really beautiful and fun morning. We returned to the parking area and were heading to a picnic table in the shade to drink some water and cool down, when a county parks employee greeted us.

“Good morning, ladies,” he said. “How did you like the hike?” Christie answered that we really enjoyed it. The ranger asked us about which trails we took, and then asked us if we had noticed some of the noteworthy things along the way. We ended up talking for about twenty minutes about the various rock formations, earthquake fault lines and groves of trees along the trail. We said goodbye and headed home, where we cooked ourselves brunch and planned our next outing.

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.

My Halloween Weekend

With everything going on these days, I had no big plans for Halloween. I envisioned another mostly boring weekend at home, perhaps running a few errands.

Christie dropped by on Thursday evening. We had both worked from home that day, so I met her at the door in a pair of denim shorts and a t-shirt. We opened a bottle of wine and sat in my back yard to chat.

“How would you feel about getting your hair colored?” Christie asked. I hadn’t ventured out since March, when the initial “Safer at Home” orders came out. I had thought about getting my hair color freshened up when salons reopened in June or July, whichever it was, but my regular stylist no longer worked at the local salon I had been going to. I really did need to do something. My hair had grown out to an unflattering dull brown, with a bit of gray that I was shocked to see. We spent a few minutes online, and found a nearby salon that I’d been to years ago.

I filled out their online registration, and the salon’s “bot” texted me right away. I told it I was looking for women’s color and blow dry/style. Within a few minutes, the “bot” offered me a choice of two stylists on Friday night, and two on Saturday morning. I picked one of the Saturday appointments.

Having made the appointment, Christie and I decided I should get my brows waxed as well. Back on line we went, and found that my regular waxing studio and esthetician were both available on Saturday afternoon. I could get both things done in one day. Christie and I finished our wine in the backyard, and moved inside for some more personal interaction.

The next day was one of the rare days that I had to go into the office. I was pretty sure I’d have the place to myself, so I put on some light makeup, a pair of skinny stretch jeans and a white t-shirt. My white bra showed through just enough to be noticed, so I brought along a sweatshirt, in case I needed it. I didn’t – I was the only one in the office. After an hour or so, my phone rang. I recognized the number of the hair salon, so I answered with a plain “hello?” in as feminine a voice as I could muster.

“Hi, Greg, this is Kimberley from the Lux Salon. I was calling about your appointment.” I was shocked that she used that name. I realized that was the name I used a few years ago, when I went to get my hair colored and trimmed. I had gone in “guy” mode. Kimberly confirmed that I wanted an all-over color. Then she explained that she had to check with one of the styling directors, because only two of the stylists were certified to give male haircuts. I blushed, even though I was on the phone. With some hesitation and what must have been obvious nervousness, I told Kimberly that I was definitely not looking for a male haircut. I went on to tell her that I wore my hair in a ponytail at work, and that I was looking for a way to wear my down and needed some help with styling. “Oh, fantastic. I’ll book you with Jasmine. She LOVES to work with guys with long hair.” She seemed excited. She moved my appointment to later that night – tonight – at 6:30.

I finished up at work and went home. I had a few hours until my hair appointment, so I had some time to get ready. I freshened up my makeup, concentrating on my eyes, since I’d be wearing a mask. I touched up my nails, and chose a pair of stretchy skinny black jeans, the distressed kind with the ripped look. I put on a black bra and cotton camisole (which made me look like I had some real cleavage) and a yellow plaid cotton shirt.

I left in time to arrive at the salon about 10 minutes early. Kimberly greeted me and asked if I had an appointment. I told her I did, with Jasmine at 5:45. “Greg?” she asked. I smiled and nodded. She showed me to the waiting area, and offered me a cup of tea while I waited.

Jasmine came out to the waiting area and found me.   “Greg?” she asked.   I nodded and smiled.  “Come on back,” she said, and led me back to her chair.  We discussed the color I was looking for, and the style.   Jasmine asked if I had a picture.  I showed her one I had found on the internet.  She didn’t seem at all surprised that I had shown her a photo of a woman with auburn hair and some bold cranberry highlights, styled in shoulder-length waves.

Over the next few hours, we chatted as she colored my hair, rinsed it, blow-dried and styled it. It was quite a bit deeper shade than I expected, but I loved it.  “Too bad you don’t have plans for tonight.  I really like how this came out,” she added.

She took me out to Kimberly to pay and schedule my next appointment.

“Let’s see…Greg?” she inquired.   I said yes, and mentioned that I had used that name a few years ago, the last time I was there. I added that I don’t really go by that name any more. Kimberly offered to merge the old account with the one I had just created to make this appointment, as “Gee.” As she did, she noticed my address. “I know where that is.   I used to work near there.”   She explained that she had worked at a café down the street from my house. I had been there often.

I handed her my card, and she complimented my nails.   I wished her a good weekend, and left for home.   Jasmine was right – I wished I had somewhere to go.

Saturday was warm, so I chose a pair of denim shorts to wear for my waxing appointment. I was wearing a beige thong and bra, and I picked out a bright orange patterned top to wear. I kept my makeup light, since Claudia would remove some of it to wax my brows.

I got to my appointment a little early, to sign in, fill out some forms and get my temperature taken. I had to wait outside, but it was a really nice day, and there wasn’t a lot of foot traffic on the sidewalk in front. Claudia came out and brought me back to her treatment room. We had a nice chat about how long it had been since we last saw each other. I couldn’t help notice that as she worked, she leaned against the table and in doing so, pressed her thigh firmly against my elbow as I lay on the table. I’m not sure if she did that consciously, but it was kind of exciting. She did a wonderful job on my brows, and filled them back in with a brow pencil when she finished. “Is there anything else I can do for you today, Gee?” she offered.

I asked her if she wouldn’t mind waxing the back of my neck. I had noticed at the hair salon that I had a few random hairs back there. She had me hold my hair up, so that she could apply the wax. “Why don’t you take your shirt off and lie down, so I can really clean these up,” she said. I took my top off. I realized that even though she had waxed my back and shoulders in the past, I had always removed my bra in the car. Here I was wearing one in front of her for the first time. Claudia didn’t mention it, and waxed the back of my neck and upper back. “Perfect,” she announced, and had me get dressed.

Late that afternoon, I started thinking about going out for Halloween. I was skeptical – I hadn’t really been out since the shutdowns began. But I had a new hair color, a new hair style, freshly waxed brows, and a I felt a kind of desperation to go out. Christie had gone out of town for work, so if I went, I’d be on my own.

For some reason, I was feeling bold. It was Halloween, after all. I haven’t used that as an excuse to go out dressed, except for the occasional party I’d gone to with Christie, but this year felt different. I picked out some of the things I’d gotten but never had the daring to wear. I did my makeup a little bold, with a lot of emphasis on my eyes. I even added false eyelashes. I settled on a kind of “biker chick” look. I wore my black thong and bra, fishnet tights, a sheer black bodysuit, a pair of black bikini bottoms, black ankle boots and a leather vest I’d inherited from Christie. I added a black leather beret, and a leather choker.

I decided to go to a local tiki bar that I knew had outdoor seating. It wasn’t crowded, and it was thrilling to be sitting streetside wearing as little as I was. There were a few other people in costumes, and most people stayed for a drink or two and moved on. I decided to do the same.

I went to a second place that had a huge outdoor patio. I had to show my ID, but the security guy didn’t seem to care that I looked not at all like my driver’s license photo. I found a tall table for two, sat down, and ordered a drink. The patio grew more and more crowded as the night went on. One woman complimented me on my outfit, and a couple of guys came over and chatted with me for a bit, but as the crowd grew, I got more uncomfortable, and left. Still, as I drove home, I though about what a thrill it was to be dressed as I was, out on my own, even if it was Halloween.

Surviving the Shutdown, Part 2

Last week, while working from home at my “real” job, I got an email from the head of the company. They eliminated my department. Fortunately, I kept my job.

Since mid-March, I’ve been working at home. I’d been working five days a week, and only going in to the office occasionally, until I (and most of my colleagues) received furlough notices. I went to three days a week, with the corresponding reduction in salary. I found out that I was lucky; to make ends meet, the company laid off quite a few people were entirely.

My friend Helen, a CPA, surprised me a few days later and helped me out hugely by hiring me as her assistant for two days a week. I’d done this before, every year during tax season, which was always Helen’s busiest time. At Helen and Christie’s direction, I’d always done that in women’s clothes. I’d always considered it a fun challenge. For the past six months or so, I’d been working one or two days a week at her office, in women’s business suits or dresses. Aside from my first day, for the most part, the only person I interact with is Helen.

Anyway, last week’s notice was a shock. The email itself was brief, and didn’t say what was going to happen to those of us in the department. Then Lauren called.

Lauren is a colleague of mine, and although she worked in a different department, we were pretty well acquainted. We’d gotten to be close friends after we traveled to a convention together about four years ago. She knew that I wore women’s clothes; in fact, we’d gone out a few times that way.

Lauren explained that when the company reassigned those of us in my department, she’s lobbied to get me into hers. It was a nice step up for me. Lauren’s department worked on a wide variety of projects. I would be doing few, if any, sales calls or warehouse work, and her office was in one of the company’s newest buildings. Lauren suggested we get together to discuss the move, and arranged to meet on Saturday at a local pizza place that had a large outdoor dining area.

I knew Lauren expected me to dress up. It was a beautiful day, so I decided on shorts and a light top. Christie had texted, as she does every day, and let me know we’d be wearing blue that day. That meant a blue thong and a lacy blue bra. I didn’t want the bra to show, so I chose a blue sleeveless cotton blouse, and a pair of white denim shorts. I did my makeup and nails, and headed for the pizzeria. Lauren looked gorgeous, in a blue floral sundress and sandals. We ordered salads and a pitcher of sangria.

We talked for a long time about work, and who had been furloughed, and discussed the changes in the organization. I was still quite flattered that Lauren worked hard to get me into her department. She updated me on what she’s been working on lately, and we talked about what I would be doing. Like everyone, we’re all working mostly from home, and going in to the office only when necessary. The company put strict limits on how many people could be in the offices at any one time.

Then, over lunch, as we continued to talk, Lauren asked me something I wasn’t prepared for.

“Would you like to come to work as a woman?” she asked, reaching across the table and touching my hand. Unlike Helen, she didn’t know Christie, but I had told her everything over the course of our friendship. She knew how it all started, how I wore panties and a bra every day, and how I dressed as a woman. I really hadn’t expected, though, her suggestion that I come out at work. “It wouldn’t have to be a dress, if you’re not comfortable. You could wear dress slacks. Whatever you like. I just want you to know that I’ll support you,” she explained.

“I never really thought about that,” I replied. “I had fantasized about it, but never really considered doing it.”

“But you dress to work with Helen, right?” she asked.

“I do dress to work with Helen,” I answered, “but that started with Christie and Helen a few years ago. It was just something fun that we did. I also don’t really know anybody there, and there’s really never anybody around except Helen.”

Lauren thought for a minute, then asked “Gee, honey, how long have you been wearing panties and a bra?”

I thought for a moment. “Oh my gosh,” I replied. “It’s been almost exactly six years.” It was September of 2014 when Christie discreetly handed me her panties at a neighborhood happy hour and directed me to go to the restroom and put them on.

Lauren and I talked for quite a long time. My head was swimming by the time I got home. I had never been so honest with anyone besides Christie. We talked about how nervous I was at first, and how thrilling being challenged can be. I admitted that I never felt forced to do anything; I felt rewarded for doing things Christie wanted me to do.

I don’t really know how I’m going to answer Lauren.

Surviving the Shutdown,Part 1

It was late March, a few weeks into California’s “Safer at Home” order, that Christie’s friend, Allison, put together a “ladies’ virtual happy hour.” Allison and I knew each other, but I was still surprised at the invitation. It could have been Christie’s doing.

I had met Allison almost five years ago. She had put on a co-ed bachelor party for her brother, and Christie and I were invited. We all wore tuxedos and went to a casino near San Diego. Christie had me wear a black bra and panties, black stockings and a garter belt under my tux. The night ended with me having gone down on Allison’s brother in the limo, and walking from the limo with Christie, while wearing just my jacket and black lingerie. I’d seen Allison a few times since. At any rate, I was surprised to get the invitation, but glad to be part of it just the same. Like most people, my social interaction for the past few weeks had been close to zero, aside from texting and talking to Christie.

The morning of the happy hour, Christie called to discuss what I planned to wear. She decided earlier that day that we’d both wear red panties and bras, so she had me put on a pair of white denim shorts and a red tank top. She also gave me some hints as to makeup, and arranged to get together early, virtually, to make sure we both had good lighting and backdrops.

The happy hour was really fun. Allison greeted everyone with “Hi, ladies!” Everyone seemed really genuinely excited to see one another. Most of the discussion was, of course, how people were faring with the restrictions. When Allison asked “How about you, Gee? How are you doing?” I got a little nervous. I had met quite a few of these women, but not all. I replied that I was well, working from home, but had just that week been told I was furloughed for two days every week. Almost everyone was in the same position. Christie’s friend Helen, the CPA, sent me a private chat message that she wanted to call me the next day. The happy hour lasted about an hour and a half. Christie called me afterwards, and we talked for another hour or so.

Helen called me the next morning. For the past few years I’d been helping Helen at her office (at Christie’s suggestion) during her busy season around tax time. It was fun to dress up and go in for a few hours on weekends, when nobody else was around, to answer phones, file paperwork and make copies, and generally be her assistant while she did taxes for her clients. I was nervous at first, but got to really enjoy working for her.

Today, though, Helen had a different proposition. A few of the senior partners at her firm had taken the opportunity to retire, increasing her workload. All of the ever-changing loans and assistance programs complicated things, too. She explained that she really needed help, and was authorized to hire someone. It would be for two days a week, since the accountants were working alternating days at the office, to minimize contact. She wouldn’t take no for an answer, and in truth, I needed the work. We arranged to meet at her office on Friday, so I had a a few days to prepare.

I told Christie, and she came over that afternoon with an armload of business suits and dresses. She explained that she didn’t need them, since she was working from home. That surprised me. I hadn’t considered that Helen and Christie had coordinated this, but it seems they had. I was going to work at Helen’s office, but I’d be doing it a woman. We picked out a suit for my first day – a black skirt and jacket, and a sleeveless, zebra print top in off-white and black. With some minor alterations, it fit quite well.

That Friday, I met Helen outside of her office. We were met by a young woman in scrubs who took our temperature, asked some screening questions, and signed us in. Helen took me to her new office, one of the bigger ones that a now-retired partner had occupied. She showed me to her outer office, where I would work. We sat down and she had me start filling out the employment forms. “When you’re done, we’ll go see William, the IT guy,” she said.

William’s office was down a long corridor. He was young and rather attractive, and he greeted us as we came in. Helen introduced me, and William showed me to a chair in front of his desk. I sat down and crossed my legs as carefully as possible. I’m going to take your picture for your ID card, which will also give you access to your computer, and the copiers and such. You can take your mask off when you’re ready. Things got a little strange, then. He had me place my hands on my knees, swivel the chair to one side, then turn my head back to him, as if this were a photo shoot! He started making minor adjustments to my pose, encouraging me with the occasional “Yes! Just like that!” I started giggling as he took several photos. “Well,” he said, “that was fun.” I put my mask on as he printed my ID card. “What’s your favorite color, Ms. Gee?” I replied with a “probably red.” He reached into his desk and retrieved a red lanyard. “One ‘probably red’ lanyard it is. You’re all set. I’ll come by after lunch and make sure your email and calendar is set up. Welcome to the team!” I looked at Helen, who rolled her eyes and smiled. “Thaaank you, William,” she said as we left.

“He’s such a flirt,” she explained as we walked back to her office. “He like to make people smile for their ID pictures. Just look at peoples I cards and you’ll see.” She showed me hers, and she was definitely laughing in the photo. We got back to the office, where Helen told me to settle in for a while before lunch.

Helen came and got me a little after noon. We had both brought our lunches, and since it was pleasant outside, we went out to a nice, covered break area, which we had to ourselves. As we ate and talked, I relaxed a bit. I still couldn’t quite believe I was doing this.

When I got back to my desk, I found a package on my desk. I opened it to find a nameplate for my desk that said “Gee G.” Helen explained that it was common in the company to call people by their first name and the initial of their last name. “People will ask you to set up a meeting with Jim W, or pick something up from Michelle J. So you’ll hear people refer to me as Helen W. So I thought you’d like a nameplate for yourself, too.” I thanked her and set the nameplate at the front of the desk. It was a bit warm, so I took off my jacket and hung it on a coat stand in the corner. I busied myself by arranging my desk and making some copies of draft returns for Helen.

A few minutes later, William (William F., as it happens) dropped by. He had me log in to the company email, and make sure I could access my calendar, as well as Helen’s. As he was leaving, he looked at my new name plate. “Looks like your all set, Gee G. Hmm, Gee G., like Gigi.” He giggled a bit, then left.

I looked at Helen and sighed, “I thought I was too old for a new nickname.” She smiled.

Things were quiet that afternoon, which gave Helen and I time to talk. We talked about the job, at first. I told her how grateful I was, and how surprised I was that she and Christie assumed I’d be working as a woman. “You don’t want to?” she asked.

“No, it’s not that,” I started.

“Then you do want to,” she said.

“It’s definitely kind of exciting, but it’s a big step,” I said.

“One that Christie and I think you’re ready for,” Helen replied.

It’s been just over three months, now, and I’m still working for Helen.

We talked for another couple of hours, interrupted by only a phone call or two.

The Poker Game

Early in March, before we were all sheltering in place and working from home, I ran into my friend Ed.  I wasn’t planning on being out long, so I had just done some minimal makeup, put my hair into a ponytail, and put on some jeans, and a white tee shirt.  Christie had texted earlier and said to “wear white,” meaning we would both be wearing matching white bras and panties.  The white bra was clearly visible through the shirt, and it was drizzling, so I added a thin white sweatshirt top.  My nails were a subtle pink shade.

Ed and I have known each other since school, but hadn’t really kept in touch.  A few years ago, I was cocktailing for Christie at a charity event and he recognized me. We’d gone out once after that.  He was a nice guy.  I’m not sure how I would describe our relationship.  He knew about my becoming Christie’s “girlfriend,” and seemed supportive.  We were friends.  He definitely wasn’t gay, but we’d had sex twice, once after the charity event, and once after we’d been out for drinks.

Ed asked me what I’d been up to, and if I’d gone out or done anything fun lately.  I replied that it had been pretty much just work, but I did tell him about New Year’s Eve.

“That sounds like a fun time,” he said.  He was disappointed that I didn’t have pictures.  I’m terrible about pictures.

He went on to tell me about a group he’s been playing poker with.  It was a monthly game, rotating between the players’ homes.  One guy hosts, and another supplies food and drinks, he explained.  The next month, the food and drink player hosts, and another player brings refreshments, and the rotation goes on.  He asked me if Christie and Lexi would like to supply the food and drink.  “You could be the waitress,” he added.

I started out with an “I don’t know, Ed,” but he persisted.  It was his turn to supply food and drink, and he was tied of the same old chips and salsa.  I agreed to ask Christie, although I knew what she would say.  “But me waitressing…how would you explain it?  In a big group, like those big events, it’s easy not to get noticed.  Most people are too into their own fun.  This seems pretty obvious.”

“I’ll just say I won a bet with you, or something.  Please? Ask Christy, ok?”  he begged.

Christie, of course, was enthusiastic.  She checked with Lexi, who really did most of the organizing work, and over the next week, Lexi and Ed worked out the details.  It wasn’t a large group, just the seven players and maybe one or two stand-by players.  Lexi, Christie and I would set up the food and bar, but then they would leave.  I was to do the serving.

On the day of the game, Christie came over to my place to help me get ready.  I had showered, shaved my body, and washed my hair.  Christie helped me do my hair in loose beachy waves.  She also shaved my back and shoulders, just to be sure they were smooth.  Then she did my makeup and nails.  I do my own makeup most of the time, and it was quite a treat to have Christie do it.    She laid out the clothes I would wear – a short black skirt, a black halter-style tuxedo top with a bow tie, black pantyhose and a pair of low, black heels.   She loaned me one of her bras – a black halter-style lace one – so the straps wouldn’t show under my top.  I chose a black lace thong that almost matched the bra.

She drove me over to the host’s house.  The host, Hal, met us at the door.  He stared at Christie and me for a minute, and then greeted us.  “You must be Christie,” he said, reaching out to shake Christie’s hand.  “And you must be Gee.  Damn.  Must have been a hell of a bet!  Come on in.”

We came in and found Lexi in the kitchen, setting up the food.  There were a few steam trays of hot food that I would have to pass around, some other things set up buffet-style, and a bar area.  The house had a very nice wet bar.  Ed had let Lexi know what drinks the players liked, so she had arranged all of the fixings for me.  Earlier in the week, Christie had made sure I knew how to make the drinks and practiced each one.

Ed was the next to show up.  After we all greeted each other, Hal congratulated Ed, speaking to all of us.  “I don’t know how you set this up, but this is amazing.  The food and drink looks great – way better than the usual snacks.  The bar set-up is fantastic.  And, I don’t know how to say this, but your waitress looks fine!   I don’t even want to know what the bet was!”

Everyone laughed, at that, and Hal went to greet the players as they arrived.  Lexi and Christie hugged me, asked if I had any questions, and got ready to leave.

Christie pulled Ed aside.  “Take good care of her, ok?”  she asked, looking at me.

“Of course,” replied Ed.  Lexi and Christie left.

Ed looked around the room.  We were alone.  “You do look great,” he said, holding my hands.  “Just relax.  These are alright guys.  Hal told everyone it was just a bet between us, like I told him.  You’ll do fine.”

The players were starting to show up, so I grabbed a tray of various snacks and went out to the front room.  Most of the remarks were directed toward Ed, about how he really outdid everybody else as far as food and drink.  Ed shrugged it off, saying “I know some people.”

I eventually got everyone situated with food and drink.  The host moved everyone to the table, and things got a little easier.  The players concentrated on the game – they were very serious – and the two stand-by players just watched.  I refilled drinks, occasionally bringing more snacks, too.

I hung back by the stand-by players, waiting for someone to need a refill.  One of them, Tony, leaned over to me.  After making it obvious he was looking me over, he asked me “so, Hal says you’re a dude.”  The other stand-by player snickered and shook his head.

As quietly as I could, I replied “Yes, I’m…a dude.  But tonight, I’m serving drinks.”  I walked back to the bar.  Some of the players’ drinks were running low.

Eventually, one of the players cashed out, and Tony took his place at the table.  As I was making a round of the table, I felt a hand up my skirt.  Tony had slid his hand well up my leg and onto my butt.  “Excuse me,” I said, stepping back.  The other players looked at Tony.

“What are you doing, man?” asked one of the players.  Tony quickly produced a few dollars and said he was trying to put a tip into my stockings.

I set Tony’s drink down.  Hal looked at him for a long few seconds, and said “let her alone.”  The players all stared at Tony, and he eventually put the few dollars onto my tray.  I thanked him.

I finished my round of the table, and went back to where the other stand-by stood, then back to the bar.  The other stand-by followed me.  He introduced himself as Barry.

“Don’t be mad at Tony.  He’s not a bad poker player, but he’s kind of a jerk.  You do look really, um, amazing.”

“Thank you,” I replied.  “I wasn’t sure about doing this, but Ed and I made a bet, and I thought ‘If I’m going to do this, I have to do it right.  So I got my friend Christy to help me.”

“Yeah, I’m not really sure how to say it.  I mean, I know you’re a guy, Ed’s friend.  But you do look…hot.  If I didn’t know, I wouldn’t have guessed, I guess.”  He was nervous.

“Thank you, Barry.” I said.  “I appreciate the compliment.  We spent a lot of time on all this, and I’m glad it seems worth it.”
“And it was just a bet?” he asked.

“This part of it was a bet,” I replied.  “I should get back to work.”  I made my way back to the table.

The game broke up after a few more hours.  It was well after midnight.  A few of the players left me a tip as they left.

I was in the kitchen, finishing the dishes, when Hal and Ed came in.  Hal was pleased.

“That was absolutely the best.  You were great, by the way,” he told me. “You really know how to do this.  We were a little worried it would be too much of a distraction, you being our waitress, but you were perfect.”

I thanked him.  Ed looked at me.  “Ready?” he asked.

“I’m ready.  Thank you, Hal.  I’ll pass your compliment along to Lexi and Christie.  We really appreciate the opportunity.”

We headed toward the front door.  Ed reached it first, and opened the door for me.  I smiled and thanked him.  As we walked to Ed’s car, he offered me his arm, which I kind of instinctively took.  We reached his car; he opened the passenger door for me, and helped me in.  I noticed Hal was watching from the porch.

We made small talk on the way home.  Ed complimented how I looked and how I managed the food and drink.  He handed me an envelope.  “It’s from the guys.”  He explained that everyone decided to put in a percentage of their winnings, if they had any.  There was a lot more there than I expected.

We arrived at my place, and Ed jumped out of the car to open my door.  He walked me to my door, where I invited him in for coffee.

We sat on the couch for a few minutes and talked.

Ed leaned over and kissed me, stroking my thigh with his hand.  I didn’t quite know what to do with my hands, so I just put them in my lap.  To my surprise, he reached under my skirt and began to rub me.

A few minutes later, he stood up and led me to my bedroom.  I sat on the edge of my bed, undid his belt and fly, and reached into his pants, pulling out an enormous cock.  I leaned down and put it in my mouth.

“God, that feels amazing.  How did get so good at this?”  he said. I told him how Christy had taught me.  Ed stood me up and undressed me slowly.  The he gently slid me back on the bed, pushing my legs apart.  I felt self-conscious, but managed to reach to my nightstand and get a condom and lube.

He positioned himself between my legs.  I was worried about how big he was, and hoped he would go slowly.  He held my ass and hips and worked his way into me.  It was intense.  I thought of how my first time with Christie felt weird and a little frightening.  It’s something feel it through my entire body.  I describe it a tight sensation in my throat, like what you feel after a bad scare.  But it’s an exciting feeling, not scary at all.  It kind of spreads out all the way to my fingertips and toes.

I felt Ed’s body tense just before he came.  When he withdrew, he took off the condom.

“What should I do with this?” he asked, grinning.  Remembering what Christie likes me to do, I opened my mouth.  That surprised him, but he emptied the contents onto my tongue.

We lay down on the bed and cuddled, and I fell sound asleep.

I had no idea how late it was when we fell asleep, but it was nearly 9 am when I awoke.  Ed was gone, and my phone was alerting me to a message.  It was Christie.

“Let’s wear blue today,” she texted.