Dana’s Story, Part 3

After getting Dana's hopes up for his crossdressing desires, Kathy lays a wet blanket on him. For now...

A Cloudy Outlook

A blank stare from Kathy would have been putting it kindly. I walked into a pub downtown to meet Kathy for dinner after my spa day and she didn’t even come close to recognizing me. I sat down at the bar a few stools down and ordered a dirty Cosmo. Paula assured me Kathy would love my look but that wasn’t the feeling I was getting. Kathy couldn’t believe the difference my hair and make-up made. We actually relaxed a bit and had a couple of glasses of wine before dinner. Kathy started asking me all sorts of questions. “How did you like the waxing. Did it hurt? Did you tear up? Why did you get the nail extensions? Do you like the narrow tips? What are you going to do after Halloween?” I was really getting into the conversation as Kathy and I starting chatting like two old girlfriends.

Our night at the bar as two girlfriends ended in a strange way. After dinner, Kathy got me out on the dance floor, and we had fun dancing together and even joined in a cowgirl line dance. After a few dances, Kathy grabbed my arm and said she needed to use the restroom with her girlfriend. Another one of my bucket list items just got checked off. After sitting, peeing, wiping and readjusting everything, I met Kathy at the sink and washed my hands. She called me back over to the sink to help me fix my make-up. Could the night get any better?

We started back to our table when we saw two well-dressed young businessmen sitting there. I walked up and asked the blond one if my purse was still sitting on the seat. I left it there when we were dancing. Kathy was right behind me and quickly introduced us to them. Bob and Steve apologized for swiping our table. I said they could have it, but they would have to pick up our tab hahaha. “That’s a done deal Dana!” Bob shouted as he ordered another bottle of champagne. I was ready for the night to be over and us heading home, but apparently the night was young. Steve got up and asked Kathy to dance and she gave me a sheepish look before heading out for a long dance set. I figured I might as well talk to Bob instead of dancing. He was an investment banker with his friend and they just closed a big deal. I clinked glasses to his success as Kathy and Steve were coming back holding hands. Kathy dropped his hand as soon as she saw me, but I just chalked it up to too much alcohol.

We finally found our way back home via Uber just after midnight with our honor intact. When we got back, I was hoping that we would have steamy, hot sex with me dressed up. That would be yet another checked box. But it wasn’t to be. Kathy apparently sobered up on the ride home and wouldn’t say two words to me. I didn’t know if it was that she was ashamed of holding hands with Steve and giving him a good night kiss. Or maybe she had time to think about my day at the spa and hated me for it. Whatever her reason(s), she wouldn’t talk about it that night or any other night.

Halloween was there in the blink of an eye and the party was a smashing un-success. Kathy was beautiful in her Scarlett O’Hara dress and it was a lot of fun helping her with the hoops and petticoats. I decided that based on Kathy’s reaction and her refusing to have any further discussion about my dressing up, I needed to tone down my Lady in Waiting costume. I found a nice conservative black and pink petticoat that I would wear with my dress to give it more modesty. I also chose to wear shorter 2” Mary Janes and dark tights instead of fishnets, and no make-up. I still looked the part, but now I was just an androgynous man in a dress. I could see the visible relief on Kathy’s face as we were working to get everything set out at the last minute for our guests. Kathy said: “that’s a different look than we started with, I like the changes.” I gave her a little curtsy and said: “thank you, Madam.”

After that Halloween I knew that we were good together, but my “dressing” would need to be put on the back burner if this relationship would last. I never thought I would find someone that would totally accept my “hobby”, so I thought that at least Kathy had seen me and didn’t run screaming. I could love this woman forever. That wasn’t the ideal scenario I was hoping for, but I thought this was the best path for me. Halloween that year was fun. I was a little down when it was over, but after getting this far, there was no way I was getting rid of my nails or hair and who wants a bunch of once used make-up? I told Kathy that Leann suggested I keep the nails because of my work and cooking, so Kathy suggested I switch to a pale pink polish that looked natural (although not real natural for a man to have 1 ½` nail tips.) I kept my hair color and extensions and learned how to pull it all back in a high ponytail or create a braided bun when meeting with clients. Kathy liked the fact that I was not over the top feminine and she was a godsend when I needed help to shape my professional, albeit woman’s image. She even gave me lessons on a very light, professional daytime make-up look I could easily do myself.

Marriage and Work

Soon after Halloween was over and done with, Thanksgiving was looming next on the social agenda. Since Kathy had basically asked me to marry her, the next step wasn’t a secret, Kathy and I went together to buy our engagement and wedding rings. Kathy was thrilled. She had an idea in her mind of what she wanted. We ended up going to an old family friend who helped explain diamonds to us. Kathy wanted a platinum ring with a marquise cut diamond. Her tastes were exquisite and so was the price. I nearly fainted (literally) when he told me the price. Kathy took me outside to get some air and told me that was a very reasonable price. I sucked it up and went back in. “Uncle” Tony was grinning when we came back in and told me the friends and family discount was 50%! Holy diamonds, Batman! Since I was now able to afford her ring, we started looking at bands for her and me. I desperately wanted a ring to match Kathy’s and we looked at several, but nothing stood out. We finally found a very slim looking band with small diamonds for my band that would be a perfect match for hers. I told her that would always remind me of her. Awwww.

We fell prey to another Midwest tradition, wacky weddings with people you have never heard of before, all drunk at a reception at the local VFW hall. Woohoo! The very next spring we were married with a bevy of bridesmaids and groomsmen. The wedding was a typical polish wedding (lots of eating, drinking and dancing) and we closed down the bar then left on our honeymoon the next day. On our wedding night we had fun sexually. It was exciting for both of us to see her in her wedding lingerie. Kathy kind of gave me a sexy smile and asked me if I wanted to try her lingerie on. As much as I would have loved to, I knew that was a minefield better left alone. I did entertain her with as much oral stimulation as she could handle before screaming at me to stop. Another check box down (getting married) and I was really looking forward to married life.

My business took off. I had three solid clients and $500k in revenue my first year. As the cash flow was considerable, my success allowed me to narrow my focus even further. With my background in finance and systems, I was able to shift my marketing to highlight the critical appointments that corporate CEO’s craved. I also started to shift my marketing efforts to maximize my limited bandwidth. On a call with my best client I put forth: “Ruth, you know I can help find your key executives, I’ve already found your CFO. I love helping you build your team, but I have a favor to ask, I want to focus my efforts on female C-level appointments. I have a strong urge to try to help break the glass ceiling for women, but I need your help to network with the right women.” Ruth Steel became my first champion and she discreetly introduced me to her inner circle of friends.

I had considered all of the women I was meeting with. They were determined and polished, but they all exuded a certain feminine aura. They were a confident bunch and I admired what they had accomplished. I discussed these qualities with Kathy and asked her help in my approach.

I wanted to subtly alter my image to even further help my relationships with these powerful women. Kathy was thrilled when I asked if she could help me. With her background in fashion and her normal everyday professional look, I was hoping for miracles. I also took this opportunity to explain my business model and my target audience to her to get her advice. “Kathy, you’re the clothing and fashion expert, how can I come across in a less-threatening way to these powerful women?” Kathy jumped in with both feet “I’ve got some great ideas for you. I’m so proud of you for helping women get ahead!” We went to Lord and Taylor’s flagship store and Kathy found me a “PS -personal shopper” to help. Kathy suggested women’s suits as a starting point. The PS – Natalie, took me to a dressing room set up for me. Natalie first wanted to measure me. I was starting to experience an out of body feeling. I had wanted to do this as long as I can remember, and Kathy was leading the charge as I was shooting down this fast-flowing estrogen river with me enjoying every second.

I was fairly easy to measure, hips 33, waist 29, chest 34, inseam 28. Natalie was out and about looking for suits when Kathy came back to the dressing room. “Dana, with the new image, I think it would be a good idea to start wearing new foundation garments as well. Would you be uncomfortable wearing some pretty things underneath it all?” “Kathy, you’re the expert. If you think I should be wearing bras and panties, that’s what I’ll do.” Hahaha

I left L&T that day with enough outfits to last me a month. I was now truly in seventh heaven. My wife had just taken me to buy a new professional woman’s wardrobe. Who was I to object? She insisted on proper lingerie to start with. Thank goodness! From now on I would only be wearing women’s lingerie every day. I was now also liberated to start my shoe collection. What first? I certainly needed pumps and kitten heels for my suits. I wanted booties and flats and even a pair of stilettos. Of course, I needed running shoes, casual shoes and sandals for around the house. Kathy was right there every step of the way, offering her advice and expertise. I was determined to master wearing high heels. I loved my shoes, especially the heels.

My first business meeting after our shopping trip was a coffee meeting with Samantha Thompson to discuss a new project she had. Samantha was a sharp Mechanical Engineer/MBA who had earned her way to the top. In the process she was able to elbow her way around and through the old-boys network. It was exciting to work with this dynamic CEO that was blazing new trails for women. I wore one of my new suits, wearing the pants version with a silk blouse and low sling-back heels and all the jewelry. My new woman’s Rolex looked professional, especially with the diamond studs in my ears.

I had met Samantha years ago when I was working with the big consulting firm, and we hit it off immediately. I had a real empathy for her uphill gender battle as I nurtured our friendship over the years. At the time, she was one of dozens of engineering managers at her manufacturing company. Unfortunately (but ultimately, fortunately) for her, she was assigned a very difficult problem on a sink or swim basis. This was a high visibility project that had the C-level folks scratching their heads. She had to discover and fix out of control scrap rates at a plant in Poland that was losing money hand over fist. It was a critical component manufacturer for one of the prestigious German automakers and her company couldn’t shut it down even if they wanted to. Samantha needed to identify the problem and stop the porous bleeding of cash. Quickly!

I told Samantha I would help if I she wanted me to, but she said there was no money in her budget for a consultant. I asked her “can a friend offer their help for free?” I had so many frequent flyer miles that I upgraded us both to business class and the 10-hour flight didn’t seem too bad. Since we were able to sleep in the reclining beds in business class, we got to her plant refreshed and ready to go. After we walked into the first ‘all hands-on deck’ meeting, we got down to business. Samantha and I had plenty of time on our flight to review the monthly financial statements, but nothing raised a red flag. After the introductory meeting, we got right to the plant floor to examine the processes. The processes were so out of whack, it didn’t take a genius to fix them. We were able to document everything for her report. The plant manager was very appreciative of Samantha’s support. He was worried about being closed, but once we went over our observations and recommendations, he was breathing much easier. On our way back stateside, we were able to put our heads together and formulate a proactive action plan that would turn out to be a template for her to use over and over again. Samantha was praised for the miraculous turnaround at the plant and her star went into a meteoric rise.

Back to our meeting in the present. After pleasantries, Samantha commented that she had never seen my new professional look but was very complimentary. I laid out my unique business plan. I told her about how Kathy is my fashion designer and had put together my wardrobe to present a “softer” image. Samantha had a suggestion and a challenge for me. Her suggestion: “Ditch the pantsuits Dana, it’s too casual for the executive level. You need some power suits with pencil skirts, sister!” Don’t I know it! I’m telling Kathy!

As I awaited her challenge, I quickly scanned the Gantt chart on her office whiteboard. Unfortunately, I knew the question before she asked. Peter Johns, a talented program manager had missed virtually every gateway on his project. I brought Peter to the company years ago and he began as a wunderkind, but that had obviously changed. I asked Samantha if she could hold off on any action with Peter so I could meet him the next day for lunch. I told Samantha I had a possible solution I would present to her tomorrow after lunch with Peter.

When Kathy got home, I couldn’t wait to excitedly tell her about my meeting. I had reconnected with Samantha and she needed my help again! When I told Kathy about Samantha’s recommendation she said “that’s what I told you! No more pantsuits!” Fortunately, most of my new suits came with both pants and skirts so I had still had a functional wardrobe, I just needed to wear more skirts! And dresses! Oh dear me, whatever will I do?

The next day saw me wearing a deep blue St. John knit, with pearl embroidery. It was a beautiful jacket and matching skirt. I wore one of my crème colored silk blouses over my blue bra and lacy camisole. I couldn’t quite understand Kathy’s glee at my appearance, but she was beaming like a proud mother hen over me. The lunch meeting went as expected. Peter looked like crap warmed over. He was known for working long hours, but this was ridiculous. His wife Teri got bored waiting up for him and had an affair and left him. The divorce devastated him, and he turned to alcohol. I know the guy was hurting but I had to try to wake him up. “Peter, you’re on your last legs here. If you don’t take control of your life, you won’t see another birthday. Get some help! After our meeting I gave my recommendation to Samantha: “Get Peter help for his depression and alcohol dependency. At the end of 30 days, either he turns his life around or you move on, either way you’ve done the right thing. The rest is up to him. If he turns his life around, you will have the wunderkind team player back on your side forever.”

The rest of my recommendation: Talk to Julie Corsair. She is an up and coming Program Manager at a competitor but is hopelessly buried under a mountain of old-boy management. I set up the meeting the next day and they hit it off right away. Julie was re-energized to work in Samantha’s group. Samantha now had another dynamic team player she could mentor and easily build a new program team around. You can’t have too deep of a bench when working with budgets in the billions and razor-thin margins. When I handed my invoice to Samantha, she winked and said she would never forget Poland.

Shortly after the wedding, Kathy found out she was pregnant (yes, it was mine too) and we were thrilled as this was a shared goal of ours. We had found out we were both fertile and virile, respectively. We went to all the doctor visits together and immediately changed our diets to “pregnancy healthy.” Kathy and I had been working out together and kept this up during the pregnancy, although we changed to focus on a yoga and flexibility workout. “Dana, I couldn’t imagine a better pregnancy, I really feel we are partners in this.” “I agreed whole heartedly.” The only thing that could be better would be if I was the pregnant one! We went together to the Lamaze and La Leche meetings, but most times I seemed more interested than Kathy was. Our friends kept telling us that we had no idea what was coming. A few weeks before the due date, Kathy started experiencing difficulties and was confined to bedrest. Of course, I was her nurse maid 24 hours a day and we made it through the delivery with no other complications.

End of Part 3