Dana’s Story, Part 2

Dana heads out into the real world, still looking for an outlet for his CD. Enjoy

The Real World

The end of college was greeted with a blast of real-world shock. I had secured a job working for one of the top consulting firms in the world with my Bachelor of Accounting and Computer Science Degree with High Honors. I loved the intricacies of breaking down seemingly unrelated, complex problems to their core. This generally gave way to an involved analysis of systems or processes or both. All of these results fed directly into several algorithms I had created to route the yes or no answers into action items.

More often than not, the solution was not hard to identify once you looked at the component pieces. My OCD brain loved to create corrective action plans to correct those problems with easy to follow, clearly defined, follow through actions.

The world of consulting at that time was pretty much dominated by males. The travel was 100% and was exciting for a short while. But it got boring pretty quickly going from airport to cab to hotel to client, back to hotel. I did like the way that I was racking up frequent flyer miles. That made my vacation planning much, much easier. I took exotic vacations to get totally away from the US to spend time on the beaches of Paradise Island or one of the Caribbean Cruises. These trips recharged my lifeline batteries. Unfortunately, it also made me reflect on the enormous relationship vacuum in my life. However, I just loved playing golf in remote settings in my cute skirts and sleeveless polo’s. (wink, wink)

After five years, I had more than enough of the rat race and tearfully told my boss I was leaving. I enjoyed working for Thomas and made him look good on budgets and time reports over and over again. I loved the work I was doing, too. I was thrown in the mix to find and solve productivity issues in all sorts of environments and machinery. I cringed as he looked like he had lost his best friend. “I was grooming you to take over for me,” he lamented. “I don’t want to take over for you, you’re 40 years old, divorced and lonely.” I never looked back. I was 25 and ready to take on the world.

I had made some really good friends in the company, but I wanted to work for myself. I was living by myself in a loft in the downtown area and began reaching out to the business contacts I had developed. I’d come up with what I thought was a unique business initiative and wanted to discuss it with my new friends. I received invaluable feedback on how to temper my appearance to make it less imposing. I also enjoyed the stability in my life and the opportunity to make it on my own.

Soon after that I started in earnest on my marketing campaign for ‘Butterfly Consulting.” I quickly came across the major objection I was expecting: “Dana, you know we think very highly of your abilities to identify and solve our plant floor productivity problems. But we can’t afford to take a chance on hiring just little old you, not the big old consulting firm.”

My contact, Robert Plaizic, was explaining his company’s internal process for vetting new suppliers. I took this chance to give Robert a real career-changing opportunity on the project I was angling for. If Robert would give me an exclusive project, I wouldn’t charge him a cent for the first part of the project, providing he would he agree to a commitment of five more assignments over the next year. It was really a win-win, no-lose for him. If ‘Butterfly Consulting’ succeeded, he would look like a genius to the board. If I didn’t succeed, he could always blame it on me, just a trial basis, and no money changing hands.

I told him I would personally complete the project from beginning to end and I gave him a full guarantee that if his company didn’t like my work at any time, I would refund his monies. “We have a deal, Dana! Based on your previous work for us, we are looking forward to seeing more of the same results.”

I was over the moon! This client would provide the initial cash flow to support my blossoming company and give me a point of reference with other clients. I just had to go out to celebrate and called a few good friends for a night out. We had a blast, starting out at the Casino but ending up a little bar called Marilyn’s.

Kathy and Crossdressing

I met Kathy at Marilyn’s Bar at the end of the night. She was a college grad about my age, with a very down to earth attitude. She came to the bar with her friend Shelly, whom she roomed with at the time and who was one of my good college friends. Kathy was an area manager at Lord and Taylor after getting her college degree in retail management. We hit it off famously and I felt she was someone I could see living my life together with…except… cross-dressing.

I put those thoughts aside as I had a long discussion with Kathy about the direction my business was going in and she had some great ideas on presentations. I loved her creativity and spirit.

I was what you would call a passive cross-dresser at that time. I’m pretty sure no one else knew about my hobby and I never, never, took any chances. But who knew? Surely my mom, at least. I kept my feminine “Dana” tucked away for safe keeping. The feelings never went away after my first experience with my mom’s girdle. I don’t know if that was because it was my mom’s girdle, but that first experience is forever etched in my memory banks. There were many other instances where I was able to at least partially dress-up before college. I also experienced more than a couple of awkward moments when Mom caught me, but she never said a word except to tell me to do a better job of washing the make-up off my face. I always wondered what she was thinking. I never had a negative vibe, but I always wondered. If I could go back…

College was a slap in the face regarding privacy. As soon I found myself living in close quarters with a roommate in a 10x12 college room, I knew there no room for my hobby at all. That environment doesn’t leave much alone time and certainly no privacy at all. Consequently, my dressing was non-existent during my college days. The only exception was my time with April and the Chi-O girls.

Kathy and I quickly became good friends and then lovers. Kathy now had her own place which I loved with all of her feminine touches. One night after we went to a particularly exciting hockey game and were headed back to my loft, Kathy looked at me with starry eyes and said: “Dana, you and I were made for each other, where are we going from here? I wanted to ask her to marry me, but I had a big secret I needed to share with her so it would never separate us. “Kathy, in my heart of hearts, you are the perfect woman for me, but I want to follow in our parent’s footsteps and be together, forever, no matter what.” We have been together for only five months, but it feels like I’ve known you my whole life. Would it be alright with you if we postpone this talk until Thanksgiving?

“Of course, my love. Love is patient!”

We were just entering the fall season in the Midwest with all of the leaves starting to turn color. It was a spectacular fall color display by mother nature. As we were driving a little north of the city to visit one of our favorite Hmong restaurants I said to Kathy, “What do you normally do for Halloween?

“I usually go to one of those lame parties at one of the Casino’s, how about you?”

“I’ve been out of town the past five years working each Halloween, so I wanted to do a big party this year at my loft. What would you think of helping with something like that?

“That would be awesome honey, do you have any idea for costumes?”

This exchange is just what I was hoping and praying for. Even though I loved Kathy, I didn’t want to propose to her without having at least a little understanding about my hobby of “dressing.” “Kathy, I have an idea that I just saw in a magazine I would like to try with you. At my party, I would like us to both be French Maids in disguise so no one will recognize us.”

“That sounds like a lot of fun dressing up, but who is going to be the host to lead the party”

I said, “I didn’t think of that, but maybe instead you could be a Countess, and I could be your Lady in Waiting.” I held my breath after spitting out my real desire to her. I would be devastated if she just shut me down, but for whatever reason, she seemed to warm to the idea. I needed to know if my dressing would be an insurmountable obstacle for our marriage. I knew I should just tell Kathy, but I thought if I showed her, she would at least give me an honest reaction.

Kathy jumped into the preparations for Halloween with a laser focus to bring this off successfully. Since I was living and working from my loft, it was much simpler for me to arrange the catering, music, decorations and libations. And of course, my costume.

We ended up finding a Southern Belle outfit for Kathy. We made the rounds of several resale shops and lucked across a gorgeous old gown someone had just donated. My costume was a little more complicated. We went to an actual uniform outlet, but they didn’t carry the French Maid outfits. They only carried the more functional uniforms for maids or serving girls. I so much wanted one of these uniforms. I told Kathy kiddingly that we should consider getting one for me to get into the role for the party. She was delighted at my words and immediately said I needed at least three if I was going to be her maid before Halloween. “Whatever do you mean by that, Mistress?” Then I made the best, deep knee bending curtsy I could. Kathy was holding her sides laughing along with the saleslady. The two of them proceeded to find undergarments, stockings, and accessories to add to the outfits.

I was running headlong down the path of showing my love my delicate side. I was scared to death but hoped upon hope that things would work out. I realized I would need a trip to a salon to complete my look. Kathy told me she would make an appointment for me this week. I was a little uncomfortable going to Kathy’s salon because everyone would know her and look at me funny. But then she told me that her salon has quite a clientele of cross-dressers and trans girls. Is such a place real? OMG! I knew I would be in good hands, despite my misgivings.

Salon Day Disaster?

On Wednesday morning I was eagerly anticipating my appointment at 8:30am at the Gurlz Salon. Well the naked truth is, I don’t think I slept more than an hour that night. Janine met me at the reception desk and said: “Hi, you must be Dana. Paula is so excited to help you today!” Kathy hadn’t actually told me what she had arranged for me, but I thought that whatever they would do is 200% better than what I could do myself. I hadn’t cut my hair since turning in my resignation, so after 6 months, Paula said “your hair is virgin territory for me Sweetie. You also have plenty for me to work with. Kathy explained your costume as a maid/lady in waiting and had a great suggestion for your hair. But first things first. Kathy has you scheduled for a full-body waxing to begin with Olivia.”

“Oh no, I faked a frightened exclamation. That sounds so painful!” Secretly, I was on Cloud 9. I have wanted to wax my body since forever, but now my girlfriend was telling me to get it done. The waxing was exquisite. Painful yes, but after the glass of wine and the endorphins doing their thing after the pain, I literally was giddy when Olivia finally got through with me. “I don’t think I’ve ever waxed anyone, especially a man, who thought that was fun”, she said. I replied: “You only live once. I want to live life to the fullest.” I was smiling ear to ear. I can now check off: ‘full body waxing’ from the bucket list.

After Olivia was done with me, I was given back to Paula. She had Chantal come over to take me to wash and condition my hair. This was another first for me. Having this ebony goddess shampoo, condition and message my scalp was sheer ecstasy. “I think it’s brave of you to go through all of this for your girlfriend,” she said. “Wait until you see yourself with a lighter look and extensions, you won’t even recognize yourself!” I was so glad I had put on tight panties after the wax or I would have a big problem. I have light brown hair and green eyes so putting highlights and extensions in would be a dramatic improvement. I couldn’t wait. “Kathy is the love of my life and I’m looking forward to doing whatever she thinks I need.” Now, not only was Kathy now totally responsible for my feminine makeover, but all of the ladies in her salon think I’m a fantastic boyfriend for putting up with everything. I was in heaven. Pinch me. No, on second thought, don’t wake me up!

The highlights and extensions were beautiful. Paula decided to give me an easy to manage full woman’s cut but with long angle cut bangs. My long hair came down in a graduated look to the middle of my back, longest in the middle. While Paula worked her magic on my hair, Leann wheeled her cart over and got started on my nails. “They look awful, don’t they? I said as I saw a frown form on her face. “I do a lot of work on my computer and I also love cooking. They both take their toll on my nails, I whined, wawawa.” Leann suggested that although Kathy had only specified a manicure and pedicure, adding acrylics because of the beating my hands take would be a big help to me, even after the party. I tried to look reluctant, but my heart was beating so fast as I told her to give me her best. I ended up with an ombre dark pink to light pink look on 1 ½` inch silk wrapped Ballerina Tips. Yep, these will definitely help me type on my computer-not. But I had waited my whole life to get my nails done and painted, and I wanted to them as long as I could. They were so long and with the taper at the end, they were truly stunning. All the girls in the shop had to stop and congratulate me.

Paula was just finishing up my hair and we were talking about all of the changes “for the party” and I innocently asked her: “Paula, you’re the expert, am I missing anything?” I was sitting there in one their signature robes with my body baby smooth, my hair long, curled and highlighted, looking at my perfectly long, nails. I saw a huge smile slowly emerge on her face as she said: “Oh, honey, we’ve just begun! What would you think of surprising Kathy with a complete make-over?” I was having an out of body experience! What would I think? Hell, yes! But I responded with a demure “do you think that’s too much?” I was rewarded with her “Baby, trust me, she is going to love you when we are through!” OMG

So, the first order of new business was to get my ears pierced, not once, but twice (I only had to wait since I was ten when my sister got hers pierced but mom refused to let me too). Then Ms. Dianna came over and lowered my chair and laid me back completely. Sweetie, we need to fix your brows! “But isn’t that permanent?” I said in my best whiny voice. “Oh no sweetie, they’ll grow back in no time!” Ok, how could I compete with that logic? Give me girly eyebrows too! But I carefully answered with: “Okay, that doesn’t sound too bad, I’m sure they’ll look fine.” Hahaha, bring it on!!!

“Last stop sweetie, you’ve been a real trouper. We almost feel like you are one of us since you’ve been here all day. Let’s let Maxine show you how to do your make-up and then we’ll get you out of here to go meet Kathy.” STFU, now you’re going to give me make-up lessons? Why didn’t I do this 15 years ago? But then again, this was really my girlfriend’s idea, wasn’t it? hahaha Make-up 101! I was taking notes the best I could with my beautiful new nails, while the virtues of a comprehensive skin care routine were emphasized. (Well, duh! Who doesn’t need a professional skin care regimen?) I knew that Kathy will want me to continue so that my face is nice for her, right? I dutifully purchased every skin care item Maxine used. That was the polite thing to do, wasn’t it? I didn’t want to be rude to anyone at Kathy’s salon, so I purchased a lot. Maxine knew her stuff. Even though I was presenting like a female, Maxine put me at ease immediately: “I know you’re doing this “for your girlfriend”, but I want to let you know that I’ve helped a lot of guys look good “Dressed Up”, so this shouldn’t be too scary for you. “Thank you, Maxine. I couldn’t dream of looking this way when I came here this morning. (That was actually a dream come true) but you and your friends have been so kind to me. I feel like crying, I can’t believe your salon could do all of this for Kathy and me.” Please, please keep going!

Since all of my planning had worked out so far, I was a little unprepared for the next remark from Paula. “What do want to wear out of here? We have 4 different outfits picked out for you. Let’s go next door to figure out which one is best.” I thought to myself that my Kathy is going to get the best present I can find for this experience! I picked out a bodycon red and black dress, tight fitting, that came to mid-thigh. They also had 4” stilettos for me which really put it all together. Now I was completely looking like a woman as I stared at the full-length mirror. Now I needed an answer to my question about Kathy and our relationship.

My concern was: what would the look on Kathy’s face be? Elation? Shock? Anger? Or maybe worst of all, a blank stare. I was petrified to find out, but kept my fingers crossed.

End of Part 2