I usually tried to arrive at the office around 8:30 but I decided it would be safer to go in early, around 7:30, so I could walk to my office without too many of my co-workers noticing. I also knew it was going to take a lot longer than my normal routine, so I set the alarm for 5:15 AM and hoped to leave by 7:00.
The 5:15 alarm rudely awakened me. I had a tough time falling asleep, worried about the reaction of my co-workers, and fully exposing the secret I had held inside for so long. I did have a slight laugh when I realized I needed all the “beauty” sleep I could get, and got very little.
I shaved my face–twice–and then took a shower, shaving a few spots on my arms and legs. I had arranged all the makeup on the counter near the sink the night before, along with the notes I took. I went step-by-step, slowly, trying not to make mistakes. It took about an hour, but in the end I was OK with the results. Then dressing; pantyhose, squeezing into the Spanx, bra, forms, skirt, top, heels. I donned the wig, brushed it out, and took a look in the mirror, and then took a couple of pictures to later text to Darcy, Cindy, and Alexa. I hoped they would like the look; but I know I did.
It was then I realized I should have eaten breakfast first, because I didn’t want to mess up my makeup. I also realized I was too nervous to eat breakfast anyway.
I loaded my purse–again, funny to think the words “my purse”–with lipstick, my house keys, wallet, and a few other things. I took a deep breath, walked to my car, and headed to work.
I parked in the garage under our building at work around 7:30. As I was an hour earlier than usual, I was a lot closer to the elevators up to the building, so it would be a shorter walk than usual. I sat in my car for about a minute, giving myself a pep talk that it was Halloween and this would be fun. I also realized at this point I was “pot committed” as they say on all the poker TV shows, and needed to just do it. I opened the door, stepped out, rearranged my top and skirt, grabbed my purse from the passenger seat, and walked (strutted?) to the elevators, enjoying the clicking of my heels echoing off the concrete walls and ceiling of the underground garage, and saying a silent prayer there were no colleagues waiting at the elevator.
Arriving on my floor, I walked to our area and turned on the lights, so I knew I was first in. The unofficial rule was the first person in would make the first pot of coffee, but as I didn’t drink coffee, I was spared that responsibility. I went to my office, logged in, and began my normal workday routine.
Around 8:00 I heard other voices, so I knew others in my area were shuffling in. About 10 minutes later, Wendy, one of my four staff, stuck her head into my office, asking “what are you doing in so…?” and stopped mid-sentence, looked at the name on my office, looked at me, and finished “holy crap! Who are you and what have you done with my boss?” while smiling from ear-to-ear. I just answered, “Happy Halloween.”
She asked me to stand so I did, and she complimented me on my outfit and said I looked great, and that she never would have guessed it was me. I gave her a brief summary of my weekend, and showed her a few pictures, and said she could see a couple others on my Facebook page.
That opened the floodgates. The word spread quickly, and I had a subsequent stream of visitors to my office, both singles and groups. My co-workers had a combination of smiles, compliments, and questions (most often, “who did your makeup?” and I would answer “me and Sephora”). I wasn’t used to being the center of attention, but I found I was enjoying it. A fair number of my co-workers pulled out their phones and took pictures or selfies with me.
Around 10 AM I received a phone call from Sylvia. I answered, and she said “I hear rumors we have a new employee.” I laughed and just said, “Same employee, just a slightly different work uniform.” She said she was busy but could I come to her office at 10:30, because she wanted to meet the “new employee.”
Sylvia’s office was one floor up so that meant walking through the office to the elevators and then to her office upstairs. I assumed at that point most everyone knew, so I just owned it. I crossed paths with a few who hadn’t heard, but they were all good natured. I knew Sylvia could have come to my office, but I’m sure she wanted to tease me a bit and make me walk through the office.
I stuck my head around the door, made sure she wasn’t on the phone, and then stepped into the doorway and said, “ta dah”! Sylvia just laughed and said, “Look at you! You look great! And your legs are to die for!” and then asked me to turn around, and so I did. She then told me to take a seat, and so I did, trying to be as ladylike as possible.
I gave her the 30,000 foot summary of my weekend, confirmed that Marni and I were going to start dating again, and she merely said “good for you.” She then added, when she texted me about coming in dressed; she never thought I would do it, but she was happy I had done so. I told her I was apprehensive, but I was also happy I had carried through. Besides, I just teased her, “Rule #1: Make the boss lady happy.” She laughed.
I then added about being the kid in grade school about being envious of the boys who dressed as girls for Halloween, and it was finally my turn. I also said although I liked to dress, I wasn’t interested in doing anything more than that, leaving the rest unsaid.
Sylvia then turned more serious. “We’re a progressive workplace. We’re proud of that. We want to ‘talk the talk’ and ‘walk the walk’. We attract better workers that way.” She then asked “whether I planned to come to work dressed again”? I said, no, I hadn’t considered it, that this was only for Halloween.
She then asked, “Be honest, would you like coming to work dressed again occasionally?”
I answered, “I’d be nervous, but yes.”
“OK. Give me a second.” She picked up the phone, and called up HR. I heard her half of the conversation.
“Hey Judy, it’s Sylvia. I’ve got an employee who needs a second ID badge. Can I send her down and get her photo taken for the new ID?” I saw Sylvia nodding and said “I’ll send her down in a few minutes.” She hung up and looked at me.
“Like I said, we talk the talk and walk the walk. We like happy employees. They tend to stay with us longer, and that’s good for us. You would be a great example demonstrating how our actions are consistent with our company policies. It’s a win-win; good for us, good for you. I’d also like to add you to our diversity committee, to add your perspective. Are you OK with all of this?”
I was stunned with what I was hearing, but just nodded yes.
“It’s set then. Head down to HR, ask for Judy, and they can get your picture for your second ID tag. Do you have another name you want to use?” Sylvia asked.
“No, I hadn’t thought about it,” I answered.
“Well, think of one for now, and you can always change it later” Sylvia said. “And come back at noon and we’ll go to lunch in the cafeteria. I’ve got a whole bunch of questions about your weekend I’m dying to ask. Plus, everyone needs to see how cute you look.”
“Yes, boss lady.” I stood up, and headed out of her office, but before I left, I turned and said, “Thanks. I appreciate this.” She just answered, “You’re welcome. See you at noon.”
I took the elevator down to the first floor, stunned at everything that had happened in the space of three days, from nobody knowing my secret to everyone knowing my secret.
I was good with that.
On the ride down, for the meantime, the path of least resistance for my new name was to just use my first initial. I had known a Diane, but she always went as Dee, so that would be my girl name.
I arrived at Judy’s cubicle in HR; we had known each other for at least five years. She looked at me and asked, “what can I do for you?” apparently not recognizing me. I answered that Sylvia called about a new ID. She asked for my last name. “Johnson” I answered. Finally, she matched the name and my voice, “Dave, is that you????”
I just nodded, and answered “Happy Halloween.”
She just smiled and clapped and said I looked great, and several of her colleagues poked their heads over their cubes and then walked over to see and greet me. Another round of compliments and questions and a couple of pictures, which I once again enjoyed.
Judy took a couple of official ID photos, got one that we were both happy with, and asked me what name I wanted to use, and I answered “Dee.” She said it would be ready in about an hour.
When I went to Sylvia’s office at noon, she had my new ID ready, and handed it to me. I took off my Dave ID and put it in my purse, and hung my new one around my neck, and went with Sylvia downstairs to our company cafeteria.
There were a few surprised reactions from my co-workers at who the “new” employee was with Sylvia, but the smiles I was greeted with pleased me and lessened my worries. I assumed this was Sylvia’s way of “ripping the band aid” off, and she was paving the way for me if (when) I did this again. As promised, she–and the other six at our table–fired questions about my weekend, the makeover, shopping at the mall, etc. My phone with the pictures also made the rounds, and lots of compliments.
I had one more hurdle. Earlier in the day I had scheduled a meeting at 2 PM with my four direct reports, because I wanted to see where they were with all of “this.” They were my team, and I needed to know if this was going to be an issue going forward.
We met, and I went through the short version. I considered myself a crossdresser, had been interested in dressing since I was a child, had hid it for the longest time, had the opportunity to dress this weekend, and that Sylvia had encouraged me to come to work dressed. I then showed them my new ID, and summarized what Sylvia and I had discussed about coming occasionally to work dressed, but I needed to know if that would cause any issues with the four of them. They all shook their heads or said no.
My final surprise was when Amy, the quietest and newest of my four direct reports, spoke up. “Dave, I tell all my friends about what a great boss I have and they are jealous. I tell them he treats us like adults, with respect and says repeatedly how he values our work, and how he makes it enjoyable to come to work.” She then paused and said, “If it makes you happy, I’m all in”–and the three others verbally agreed.
I said OK, I have my answer, and said thanks, I appreciated the kind words.
I didn’t get much work done that day, but it was one of my best days at work in a long time.
As it was Halloween night, I went home and changed into the floral dress I had bought at the consignment store the day before. Marni and I had arranged earlier that I would drive to their place a little after 8 and Lori and the two of us would meet Alexa at the Grove for a late dinner. In the meantime, I handed out candy to the trick-or-treaters who came to my door, with an eye out for boys who just might be dressed as girls.
The Grove was a lot more sedate than it had been on Saturday night, but there were a few regulars, and I got another round of compliments on my look. I filled in my three companions with a summary of my day, and then pulled my new ID from my purse, and told them the boss lady and my staff said it was OK with them if I came in dressed in the future. They were almost speechless, but Alexa finally asked if I was planning to do that, and I could only answer, “Probably.” Lori said “Wow” and Marni just added, “I guess that means more shopping.”
I did another set of Facebook and Instagram posts of my Halloween at the office, with a bit of verbiage and a lot of pictures. As with my Halloween post, I received an amazing number of likes and favorable comments.
Over time, I established a new monthly routine.
Our office had a tradition of going to Happy Hour at a local bar on the last Friday of the month. I decided to make that day my monthly day to come in dressed as Dee. My co-workers began to look forward to what I would wear monthly. Even though our office dress code was business casual (which I strictly adhered to as Dave), my Dee dress code was business professional–dresses, tops and skirts, or a suit. After Happy Hour, Marni and I would meet for dinner.
On the last Thursday of the month, after work I would drive to Alexa’s salon to get my nails done for the weekend. I would show my nail tech a picture of my Friday outfit, and she would pick a suitable color to match the outfit.
Saturday morning I would return to the salon and assume my receptionist duties, while doing all of Alexa’s accounting for the month, and doing the lunch order pickup.
Saturday nights I would generally have a girl’s night out with the nurses from the hospital, as they hit the dance clubs. They invited me to come along one night, and I became a regular. They were happy to have a designated driver and avoid Ubers, and I enjoyed getting to show off my club wear. Marni was also happy to have a night where she could chill at home.
On Sundays, I would still do my long run–but afterwards I would hit the mall and stores, to find my outfit for the next month, and do any other errands. Somehow my grocery shopping and Costco runs were more fun in girl mode.
Marni adjusted to having Dee around once a month. She and Lori were still roommates, but Marni and I were often overnight guests at each other’s places (as were Lori and Alexa).
Life was good.
Plus, one other change.
To accommodate my Thursday salon visit, Lori and I moved tennis to Wednesday nights, followed of course, by post-match drinks and nibbles at the Grove.
The game must go on.
You can revisit the story at : https://www.literotica.com/s/secrets-150