We arrived at The Grove around nine and it was rapidly filling up. We found a table with a few of the Thursday regulars and a couple of empty chairs. I was curious as to the reactions of those who knew the guy me. Two of them looked at me and started smiling as the light went on, while a third had a quizzical look on her face. The third turned to the others to figure out who I was, and when they said under their breath who I was, she just turned and said “Wow” and came over and gave me a big hug. The other two did the same and said I looked great.
For the first time–of many times that night–I described my day in a Cliff Notes version. They also wanted pictures with the “hot” devil–and I was happy to oblige. Then a DJ started playing dance music, and I got dragged out to the dance floor to show my moves. With the heels, my moves were definitely limited, but I seemed to be a hit.
There was a wide range of Halloween costumes for both the men and the women and the TBD, including drag queens and kings and many racy outfits. Over time I felt less and less exposed and more and more at home. The Thursday regulars bought me drinks and wouldn’t let me leave the dance floor, although after about an hour I ditched the heels and just danced in my stocking clad feet–part to relieve the ache in my feet but mostly because I found that alcohol and heels didn’t mix well for me.
After about an hour of dancing I escaped the dance floor and found Marni. I apologized for ignoring her but she just shook her head and smiled and said, “It’s your night, and you should enjoy yourself. Besides, I’m getting all the scoops on you from all your friends!” She then added, “They only say good things about you.”
And then she kissed me on the lips, and said, “It’s good to see you happy.”
She then grabbed my hand and said “come with me.” She led me to a quieter area of the bar so we could talk.
“I’m still dealing with this,” she started, and she motioned up and down with her hands– “but I think I can. I know doing this is your big secret, but I’m not sure I want to be part of the secret. I’m not sure I can handle that part of it. If we’re out together and you’re dressed up and we meet someone one or both of us knows, how would we deal with that? Are we going to be embarrassed? What about social media and your friends posting pictures of you? What happens then?
“I guess what I’m saying is I’m willing to be with you–the true you, the boy AND girl you–but I don’t think I’m willing to be ‘in the closet’ with you. I’m not sure I can handle that pressure.”
I just nodded while I tried to compose an answer. Given the alcohol I had consumed I was somewhat buzzed and my mind was spinning. Marni was ok with me dressing, and going out with me dressing. But was I ready to show EVERYONE a side of me I had hidden for so long???
I suspect the alcohol helped my decision making process, but I decided the reward of having a second chance with Marni exceeded the potential cost of coming out.
“Thank you for being honest with me. Thank you for giving us a chance again. I’m willing to come out of hiding,” I answered. “Stay here. Give me a minute.”
I hurried over to my purse–I giggled at the idea of my purse–and took my phone out, and walked back to Marni.
I opened the Facebook app and wrote a quick paragraph about my day, added that going out on Halloween dressed had been a desire of mine for a long time, and thanked Alexa and the team at Alexa’s salon. I added five pictures of me, both from earlier in the day, and one of Alexa, Lori, Marni, and me. I tagged them all, and handed my phone to Marni. She read it quickly, and nodded.
“Are you really ready to do this?” she asked.
“Yes, but hit post before I change my mind” I said.
I then posted the same pictures to Instagram, added a few comments, and posted them too.
Marni then took my hand and said “come dance with me girlfriend” and we did.
Half an hour and multiple dances later I dared to retrieve my phone again from my purse. A lot of people must not have a lot to do at 10:30 on a Saturday night because my posts on both media had a number of comments and likes, with a number of “wows” and “you look great” along with a couple of “what are you doing with Marni?” questions. I also noted that Marni had clicked “love” on all five pictures.
While I was reviewing Facebook my phone pinged with a text from my boss Sylvia.
[OMG, you look great. I would have never guessed it was you!].
Sylvia was around 40, married to a great guy with two great kids, and an excellent boss. She was one of my Facebook friends.
[Thanks! Been a fun day] I texted back.
I added a couple of other pictures I hadn’t posted on Facebook and hit send. I then typed out; [I have to confess moonlighting at the salon] and added a picture of me at a monitor.
[LOL. You know Halloween is actually Monday, don’t you???] Followed by a smiley face.
Sobering up quickly, I texted back, [What do you mean?], and hit send.
[You can come into work dressed if you like] came the quick reply.
[I’m not sure I can do that] I typed back.
[I would be disappointed if you didn’t] followed by two frowny faces.
Shit, shit, shit, shit, shit.
I think I sobered up in five seconds flat. I walked over to Marni and showed her my phone and the texts. I was hoping for sympathy.
I got hysterical laughter.
“What’s so funny?” I asked.
“Never thought I’d have to take my boyfriend out dress shopping.”
I woke up around 10:30 the next morning a bit disoriented. I realized I was in Marni’s bedroom and hazy bits and pieces of the night before hit my memory; climbing into the car when the bar closed, stumbling into Marni’s bathroom, feeling sad when I used the make-up remover pads to remove the make-up, then stumbling to bed, and falling asleep dead to the world. I had been in no condition to drive, and my car was still at Alexa’s salon anyway.
I managed to make it to the bathroom and I noticed I was still wearing the panties from the night before. I did my business and while washing my hands noticed a bottle of ibuprofen sitting on the counter, so I took two and washed them down with a handful of water from the tap.
Returning to the bedroom I noticed a t-shirt and some sweatpants on a chair, and as they appeared to be a bit larger than Marni would wear, I assumed they were Lori’s and left for me to wear. I put them on and staggered to the kitchen where I found Marni, Alexa, and Lori drinking coffee and chatting.
Alexa spotted me first and said boisterously, “Good morning, Miss Sunshine!” I merely grunted.
Marni asked, “Want some breakfast?” and after nodding yes I found a cereal I liked, poured myself a bowl and gobbled it down, accompanied by a banana. I began to feel a bit more human. The three others talked, but I wasn’t really listening.
I finally realized one of them–I think Lori–had asked me a question. I asked her to repeat it.
“So was yesterday everything you hoped for?” she asked.
“Yeah, it was great. A fabulous makeover, going out in public dressed, dancing in a sexy dress and heels–and finding out someone I have feelings for is giving me a second chance. Doesn’t get much better than that.”
My answer was rewarded with three smiling faces.
Eventually I learned the plans for the day, which the three had arranged the night before, without my knowledge. Lori was going to take me to the salon, to pick up my car and the boy and girl clothes I had also left there. After I drove home, I would have a chance to quickly shower and shave, because at one Alexa’s sister Darcy and her friend Cindy–two of the four I had advised for their 401(k)s–were picking me up to do some shopping.
Girl shopping–because I was going to work Monday dressed. In for a nickel, in for a dime.
Darcy and Cindy arrived a little past one. They had been at the Grove the night before and they dragged me out to the dance floor a few times to dance with them and their group. I asked Darcy if Alexa had roped her into taking me out today, but she quickly answered “No, we volunteered! We love shopping and this is our way of paying you back for all the advice you’ve given us! We’re gonna have FUN!!!!”
I was dressed in a polo shirt and a pair of Dockers but the two quickly vetoed that. They said if I wanted to shop for a girl I needed to look like a girl, and that I needed to “own it.” They sorted through the clothes that Lori had donated to me, chose the Minnie Mouse t-shirt and mom jeans, and shooed me into my bedroom to change into them–and panties and a bra. I retrieved the foam inserts and inserted them in the cups.
When I finished dressing, I walked back out and they liked the look. They asked me to get the wig and my black heels. Darcy shook out the wig, and placed it on my head, and used her fingers to brush it into place. She had me sit, and applied some light foundation and some lipstick. I put on my black pumps and walked into my bedroom for a look in the mirror. I looked decent. Darcy had me pose for a couple of pictures and we took a couple of selfies together. She texted them to Alexa, Lori, and Marni, and in return got a thumbs up.
When we were in the car Darcy told me the first stop was a Sephora at the mall. She had a friend who worked there and I was scheduled for a makeover at two. They explained the makeover would help me know what makeup I needed and the steps to do everything. They assured me their friend Cailee who was doing the makeover was very friendly and that I would love her.
I felt a bit exposed walking into the mall with the Sunday crowds but with the company of Darcy and Cindy no one seemed to notice anything unusual about me. I guessed strength in numbers. We walked into Sephora and were greeted at the door, and were told that Cailee would be right with us–and she was. Darcy and Cindy and Cailee said their hellos, and then introduced me as Dave. Once again I realized then I would need to think of a more suitable name.
Cailee walked me to a counter with a tall stool and had me sit. I briefly told Cailee about my day before and explained I had committed to going to work the next day dressed. She just smiled and clapped her hands and said “yes!” I also added that probably wasn’t the last time I was going out dressed, so I needed to learn what I needed to wear and do, and that I had never done makeup before.
Cailee just smiled and said “let’s get going then!”
Over the next hour she went through the steps, patiently explaining everything she did, and I borrowed a pen and paper and took notes. I was smiling internally that my final exam on this test was tomorrow morning, and I wanted a “passing” grade. First moisturizer, then a green primer to offset the reds in my complexion. She did a color match for my foundation, and then showed me how to apply it using a stipple brush. Then concealer, and brushed on powder to set it all.
Next eye primer and eye shadow and mascara, then two tone powders for my brows, lighter on the inside, darker on the outside. Multi-color blush on my cheeks, and then some choices for a lipstick color. We jointly decided on a dark red, and Cailee found a lip liner to match the color. After the lipstick, she let me have a look. Not as dramatic as yesterday’s makeover, but although daunting, I thought I could possibly duplicate most of the look tomorrow–and then again in the future.
Cailee gathered all the products and as I was checking out Darcy and Cindy reappeared. They both loved my look. Cailee asked if I wanted to join Sephora’s Beauty Club, and after an initial no, I decided why not? The tally was a bit higher than I expected, but I just tapped my Visa on the keypad and the bagful of makeup was mine.
The next stop was the Nordstrom at the mall. While Cailee had been working on me, Darcy and Cindy had been looking for things for me, and they had a dressing room set up with clothes for me to try on. There were slacks, jeans, tops, and a couple of dresses, all with a business woman vibe. They explained they wanted to see what types of clothes suited me, and once they had ideas for what style worked, our next stop would be a higher end consignment shop to actually buy things–unless I found something at Nordstrom I couldn’t resist.
I spent about an hour trying on various combos of tops and bottoms, and learning my sizes. I would try something on, pop out of the dressing room, and get the reaction of Darcy and Cindy, and if around, the Nordstrom sales agent. If something didn’t fit, one of them would chase down a different size. We whittled it down to a dark blue top with a white stretchy skirt, plus a Spanx bodysuit to keep everything in place.
Then I was marched over to the lingerie area, where, somewhat to my embarrassment, I had a bra fitting. However, the specialist doing the fitting kept it all low key, and suggested three bras for me to try on, and after trying them all with the foam inserts, I found a basic black bra that fit the best. Darcy and Cindy had more fun with me looking at panties, and asking which ones I liked (most of them), and ended up buying five pairs.
Next was Macy’s for shoes, or more accurately, heels. The dynamic duo checked the close-out racks for my size, and brought them to me to try on. Most of the pairs were too small, but they found a pair of black Mary Jane’s that were work suitable, so I added them to my growing wardrobe–along with two pairs of nude pantyhose. My outfit for work was now complete, and I walked out of the mall carrying my bags full of fun new stuff.
I thought I was done, but the girls had one more stop–the consignment shop. They said I would love it–and they were right. Besides, they convinced me I needed to buy at least one dress, because I’d be going out after work tomorrow for Halloween. I ended up finding one red floral dress suitable for work, and a short dress, as they said, to wear “clubbing” with them one night. We also found a purse that suited me. The staff at the shop told me to come back any time, and thought I looked great in the dresses.
We finally finished around six. We returned to the California Pizza Kitchen at the mall and I bought dinner to thank them. Sometime during the day being out in public dressed had suddenly felt natural, and I realized I could learn to like this. I paid for our dinner as a thank you to Darcy and Cindy and the waitress said “you ladies have a good night.”
On the way to my house we stopped at a drugstore and bought some makeup wipes and nail polish remover. They dropped me off at my house–with a couple of farewell hugs–and I carried all my new toys into my house. I got a beer from my refrigerator and sat down to watch Sunday night football, postponing as long as I could to remove the makeup and return to the boy me. All I knew was that I was equally excited and anxious about going into work the next morning wearing my new blouse, skirt, and heels–and what reaction I would get.