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.
Gee's Crossdressed Life 