Dana’s story starts early in life and without a lot of drama. Although slow starting, it builds quickly then enters the deep currents that our hero(ine) finds herself floundering in. Heavy TG, no violence. This work is a fiction of my mind.

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A Middle-Class Beginning

I was the middle son of a middle-class family, living in the Upper Midwest in the USA. Although my Grandmother and Grandfather were born in England, I have no English memories or stories, sadly to say. I wish that I could relive those times with my grandmother and ask her to tell me of her history. As a young lady she was born and raised just outside London. As a young girl, she sailed the Atlantic to Canada. That is where she met and married my Grandpa. I never knew Grandpa Hudson, he died around the time of my birth. My other Grandparents were the salt of the earth people. Hard working, raising big families. I had it made.

What could happen to possibly spoil that yellow brick road?

When I was 5 years old, I vividly remember my best friend Troy telling me one day as we were heading to our respective homes for dinner “you wouldn’t believe it Dana, I found one of my mom’s girdles in the laundry basket and tried it on. It was like a nice nylon hug, hahaha.” I looked at him like he had a 3rd eye and laughed and ran the rest of the way back home.

After that, all I could think of was my mom’s girdles! I thought I was losing it. We lived in a “ranch style” house with a full basement. One of the features of the house was the laundry shoot. All of the dirty laundry tossed in the shoot upstairs ended up in one community hamper in the basement. This made it much simpler to do laundry.

After a couple of days, I couldn’t stand my curiosity regarding the girdle any longer and wandered off to that hamper to find a girdle like my friend had described. Shortly after I began searching, I found pay dirt! There was an all-in-one girdle that was exquisite. It had embroidered stitching on the outside, but the inside was a soft rubber. The smell and feelings were indescribable. OMG. I pulled it on and all at once I just stared at myself in the garment. I was in awe as the very feminine feeling as the garment compressed my waist like a giant hug. As I smoothed it over me, I realized that I needed to get out of there soon or one of my family members might wander in and wonder what I was doing.

Puberty

I grew up in suburbia, a normal American boy. Played basketball, football, golf, tennis, etc. with my friends. Being raised in a middle class, suburban neighborhood, we had lots of other kids our age we knew and played together. But once we started entering puberty, anarchy reigned! Who knew what this puberty thing would do to us? It had a profound effect on my early life as things changed drastically with my three best friends, who all happened to be girls in my neighborhood. Up until that time we played together every day. We loved playing role playing games like “House” or “Dress Up” or “Mommy.’”

I have to admit, I loved being playing with the girls. I might have been the girliest of all of us. I can’t say why what happened, happened. I’m not sure what to think of those days. It was the best of times, it was the worst of times…

It seemed like one day Melissa, Elaine, Anna and I were best friends hanging out and riding our bikes and playing together and the next day, they didn’t even know me. I couldn’t fathom what could possibly have happened. When I knocked on Anna’s door her dad answered. “Can I help you?” I was a little taken aback by his demeanor, like he didn’t recognize his daughter’s best friend! Hi Mr. Peters, I’m here to see Anna. I’m sorry, but Anna is unavailable. Good-bye Dana.

Well that was just plain mean. I would later learn in life that he was just trying to “protect” his daughter. Apparently, he was not the only one who thought that way. After the incident with Mr. Peters, my contact with my former “best friends” was just an occasional “Hi” in passing at school. Who in the world acted that way? I was a good friend one day and persona non-grata the next? I found out that the fathers that felt that way did so for a good reason. They looked inside themselves and were found wanting. But they set the rules according to their own faults, not thinking about our friendships. That was a devastating blow for me. I loved my girlfriends but from then on, I could only live vicariously through them. This meant ‘I was on my own again, naturally.’ My mom tried to console me by telling me about the differences between boys and girls, but it just wasn’t fair. How could your best friends stop talking to you like that?

High School

Notwithstanding all of the changes that puberty wrought, my public-school education was wonderful. This was mainly because my mom stayed home and was quite the mentor of my brothers and sisters and I as she worked and played with us. I played sports and was quite good because of my hand eye coordination and because I loved to play almost any sport. My mom was my idol, she was svelte and ran around with us kids every day. She even went to the beach with us and taught us all to swim. I cherished my time with my mom. I helped her to cook and clean and she even showed me how to use her sewing machine. Some of my fondest memories of my mother was of those times when we were alone working on projects or cooking dinner.

Even though I was quite good at sports, I didn’t have the killer instinct. I felt bad when I was beating my opponent. I won quite regularly, but they felt like hollow victories for me. I took a bit different course of study than many of my friends in high school. My mom was always telling me to challenge myself. I was the only boy in my typing class, but I relished achieving one of the highest WPM scores. I also took shorthand and home economics instead of “Auto Mechanics” or “Woodshop”. All of those skills were instrumental for me taking notes in college and then when computers took over the workplace. It’s not that I didn’t like working with my hands or on my car. I could change the oil, sparkplugs, brakes, even the clutch. But that was nothing compared to my pride in finishing my first pencil skirt in home economics. Since I was one of the “jocks” I got a free pass taking my “electives” without any of the accompanying bullying. I also got to know a lot more girls at my school since everyone wanted to help the “poor boy.”

College
I did quite well grade-wise in high school and graduated in the top 5 class, then proceeded to ace the SAT exam (although my friends didn’t have any clue that I was that bright). I didn’t have any other friends that placed in the top 1% of the country, but I kept that to myself and my parents. I had my choice of colleges but picked the local favorite and had a great college experience in every way. Remember this was quite a few years ago and the only STD was gonorrhea, and who was going to get that? On top of that, I lived in a co-ed dorm and few questions were asked.

My love life during this time was good. I had a couple of girlfriends in high school. I went to Homecoming, Prom, school dances, etc. Just the normal guy high school stuff. In college I had a couple of long-term relationships. I treated my girlfriends like I would want to be treated. Sometimes this came across as not very macho, but I had a real empathy towards my girlfriends. I will say that I respected the women I had relationships with. I felt a kinship with them. I hurt when their monthly visitor came, and I rejoiced with them when they experienced success. I envied my girlfriends in every way.

My senior year in college I met April and we became good friends. She was one of the few women in my major. In fact, she was the only female in this somewhat nerdy field. I had seen April for the last three years because most of our classes overlapped. Since she was usually the only female in our classes, she was generally swarmed by guys trying to date her. Senior year I was living off campus with a couple of friends. One day after classes were over for me, I headed to the local Pretzel Barrell for a couple of drinks and some comfort food. When I walked in, I saw April at a table with her laptop open. I knew who she was but had never really talked to her and didn’t want to invade her space, so I got a drink and started over to another table. “Dana! Come over here and sit with me.” What? She knows my name?

I put my stuff down and held out my hand, “I didn’t know you knew my name, Hi April.”

“Of course, I know who you are Dana. You are the smartest person in our class!” That wasn’t something I was trying to promote. “Why do you think that?” “Because your homework is always early or on time, and I’ve never heard you answer a question incorrectly in any class for the last four years.” “That’s pretty observant April, but I know something that you don’t. You are by far the prettiest girl in our whole class!” She replied in deadpan: “I’m the only girl, you goof.” Well, that too.

I had a great time my senior year with April. We were friends, but I didn’t want to put any dating pressure on the only girl in our major. So, we kept our relationship strictly platonic and ended up best of friends. She told me about all of the guys hitting on her. She had a rating system, which surprised the heck out of me. 1’s were marrying material. 2’s were great dates, lots of fun and safe. 3’s were the bad boys that all the girls fantasied about, but were afraid to meet.

I asked April where I fell in her system? I hoping for a 1, but… “You’re my BGFF, of course!” Best Friends Forever? “No silly, Best Girlboy Friends Forever.” It was the best I could hope for and we pinky swore our pledge.” Like I said, college was awesome. The best part? Greek Week senior year.

Sorority Fun

April was in the Chi Omega Sorority and I think that helped her keep her sanity in classes overflowing with too many males and too much testosterone. After we became friends, I used to spend a lot of time at her sorority house studying and hanging out. I got to know a lot of girls in her house and was generally good as a sounding board for them. One night, April got me hooked on a very girlish activity. We were finishing up our calculus homework when her sorority sister Gwen rushed in and said she was running late and asked we could help her get ready. I had kept my hair quite long in college (because I could) and many times got called “Miss” from behind. April winked at me as she shouted, “Let’s get going!”

While Gwen was getting changed, we were chasing her around the room. April was doing her hair and I’m totally flabbergasted that Gwen didn’t end up with multiple curler burn marks. I guess it’s another of those innate abilities’ girls possess that rise up in emergencies.

I was not girl, but I was assigned the task of ‘painting her nails.’ That didn’t sound insurmountable. We agreed on a cobalt blue color to go with her eyes and dress. I started out with her toes and had enough time to do them twice, even after starting over on both her middle toes (was that a sign from God?) Trying to paint Gwen’s fingers was another thing. She had long almond shaped nails which I had hardly ever seen before and she wanted them done in a two-tone look. While April started on her hair, I quickly looked up that type of nail on Pinterest. Luckily for me there were several examples and a 2-minute tutorial on ombre nails. After viewing, I suggested a graduated coloring on the nail tip and Gwen hugged me! “That would be so cool. Thank you, thank you, thank you.” I had to chase her and April around the room while they were dressing to paint her nails. “Don’t you dare smudge those nails, girl!” I was as serious as a heart attack.

We were attracting a bit of a crowd while trying our best to get Gwen finished and out the door. We had about half a dozen sorority sisters sitting on our couch and bed as I put the finishing touches on Gwen’s fingers. We got her jewelry situated and April and I put her over the top with our make-up suggestions. Finally, she got her lipstick and gloss on and headed out for fun.

That was the beginning of the absolutely best night of my college career. The sisters were plying me with alcohol and begging me to do their nails, too. I think painting your nails is about as girlish a thing you can do. I loved creating new designs and colors on everyone’s fingers and toes. One of the girls surprised me by passing around a fat Dooby dooby doo. That pretty much killed any inhibitions I had about this slumber party that I ended up in the middle of. I started putting designs on every girl’s toes and tried to outdo myself on each one, especially with the Chi Omega logo and initials. April wrapped her arms around me from behind as I was finishing the Mona Lisa on Sandy’s big toes.

“Dana, you’ve been our honorary ‘little sister’ tonight and we want you to have these special gifts from us.” April and a few other girls took turns giving me gifts to open. I felt rather foolish sitting there in just April’s nightgown and panties. I was handed the first gift- a sexy red bra and panty set! Darla, the house master at arms explained that red is a special color for new initiates. Awww, so where is my room???

The next gift was a sundress! “Dana, we have our alumni get-together tomorrow and would love for you to join us. “April, I love all the girls in your house, but I’m obviously not a girl. “Dana, relax, you are an honorary Chi O girl!

I had another great day with them as we sunbathed on the back roof-porch of their house with me in a lime green bikini!!! The next day was the get-together so I thought the best course of action for me was to get busy in the kitchen. I would at least have modest clothes and hopefully an apron to wear. When we were getting ready for the evening, April pointed out to me that I had bikini tan lines. I grinned at her and said: “finally!” We got our serving attire on and headed to the kitchen.

Darla was having none of that. She told Gwen to take me back upstairs and make me ‘presentable’, even if working in the kitchen. I loved these girls. After making me ‘presentable’, Gwen and I came back downstairs to a group applause. They all turned, so I gave my best curtsy to their oohs and aahs. I got to hang out with the Chi O girls all senior year and it was wonderful. April landed an assignment in Hawaii and I asked if I could be her assistant. We had a tearful good-bye but remained friends forever.

End of Part 1

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

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

Dana’s Story, Part 4

Dana and Kathy are settling in to married life, and opportunities abound for Dana’s CD.

Coffee Club Wives

The impending birth of our daughter also brought another significant change. We decided to buy a fairly big colonial home with a built-in pool in a nice school district. It was at the end of a cul de sac in a nice western suburb close to the airport and two major malls. Our neighbors were typical traditional nuclear families. It was comfortable for us as newlyweds to be near like-minded people. Not that we were all the same faith, or color or political persuasion, but by and large, we were all trying to establish our own family roots. We soon found out there was an epidemic in the neighborhood that we unknowingly stumbled into. There were currently three other wives that were all due to deliver within several weeks of Kathy.

While Kathy was off her feet, she was busy directing the final touches for our nursery. It was a wonderful time with Kathy and I starting a family together. Finally, the big day arrived, and Kathy safely delivered Emily. What an amazing event. At recovery, Emily was given to Kathy to start her nursing. It was a beautiful sight watching mother and child bonding. I could only imagine myself in Kathy’s shoes with our newborn. Unfortunately, nursing didn’t work out for Kathy and Emily. Kathy stopped after a few weeks because of her cracked and infected nipples (ouchie, ouchie).

However, that wasn’t the end of the world (at least my nipples were ok). It even allowed Kathy to return to work. I actually think that me taking over Emily’s day to day care and Kathy ending her breastfeeding routine helped her more easily get over the post partem blues that some women experience. Since I was working from home, I adjusted my schedule so that I could work time blocks that alternated around Emily’s schedule. The pregnancy epidemic had left our little neighborhood with multiple babies. That meant it made sense for us “wives” to get together for coffee. This was the scenario Kathy and I were hoping for and we enjoyed time together with our new friends for potlucks and bar-b-q’s over the weekends.

After recovering from her pregnancy and delivery, Kathy and I resumed our workout routine. We changed to different aerobic workout tapes and Kathy gradually worked back into her pre-pregnancy figure. I decide I would support her fully and our workouts got a little competitive. As we worked out every other day to start our mornings, both of our figures were lithe and healthy. After fully recovering from the breastfeeding fiasco, I did my personal best to restore the vitality to Kathy’s nipples. She liked to reciprocate on mine and we had some passionate time together (between feedings for Emily).

I quickly insisted that Kathy sleep through the night, since there was no sense in both of us getting up for late night feedings. This was my absolutely favorite time of the day with our little girl. I didn’t mind getting up in the middle of the night to answer my little girl’s cries. I would first wipe her clean, change her diaper and smooth the lotion over her bottom. Then we would make our way to the kitchen to warm up her bottle. Emily had such a sweet look on her face. She was tired and hungry and looked at me with her big brown eyes that would just melt butter. I cherished these times that would never come again. After her milk was ready, I would take her to our recliner/rocking chair, and we would just mellow out together while she drank her bottle. More than once Kathy had to wake me to put Emily to bed when Kathy got up in the morning.

My fellow neighbor’s wives with children were immensely helpful when I needed to run out for a couple of hours for client meetings. In return I organized many of our neighborhood activities. I wanted to keep in shape, so we started out with a stroller brigade. We were pretty imposing as we fast-walked our strollers around the surrounding area. This in turn gave way to a mother/child yoga class. The other women in our group were dynamic non-trophy wives who had a bit of a competitive streak in them as well. Our activities started to look like some high-end exercise video because of the outfits the other wives kept showing up in. I jumped on this obvious opportunity to expand my feminine wardrobe further by appealing to Kathy’s sense of fashion. I told her that I was having trouble keeping up with the coffee club lady’s fashions and I didn’t want Emily to feel bad about it. Kathy again came to my rescue and the next day brought home five new workout outfits for me as well as a couple of cute leotards for little Emily. As soon as Kathy got home from work, Emily and I had dinner for her and afterwards, we took an evening walk so that Kathy could hold and talk to Emily. “Dana, thanks for taking care of everything, you don’t know how much it means to me.” Kathy, I love you. I would do anything for you and Emily.”

Kathy continued to keep her eyes open for new suits to add to my professional woman’s wardrobe and I felt that was a huge edge for me. I explained my new model to potential clients as Laura and I met with them together. Spring had arrived early, and Easter was a family tradition on both sides. Kathy bought mother and daughter dresses for her and Emily and we had a great brunch with the neighbors afterwards. We both felt I should just go with an androgynous look. Both grandparents were over the moon with us and Emily. I was glad we were over an hour’s drive from both sets of grandparents, so we had very few unannounced guests.

Butterfly Consulting continued to grow and prosper. I had hired three women over the last four months. I met them through my networking, and they were a godsend. They all worked remotely (from home) to do research after we had a clear definition of issues. We all got together at my house for lunch every Friday to review our activity. These women were awesome. But they didn’t want to work outside the home, so our arrangement was a win-win. Two of the three women had young daughters, similar in age to Emily, so our get togethers also turned into play dates for the girls.

I wanted to figure out a way to include Cori, Laura, and Kim into the success our business was experiencing. I initially paid each of them whatever they thought was reasonable and shortly thereafter I brought them all up to the same, fairly high salary level. Although I paid them a salary, their combined efforts helped me triple my business while keeping the service level high to our clients. I told Kathy of my dilemma and asked her opinion.

“Why don’t you give them a bonus or profit sharing?”

“How much do you think is fair?”

“My last quarterly bonus was $2,500, I’m sure they would appreciate that.”

“I looked at her a little sheepishly and replied: “I was thinking more like $25,000?”

“What are you talking about, that’s like giving them a new car!” I looked down and shuffled my feet a little and fluttered my eyelashes, adding, “I did consider giving them all company cars. Do you think that’s too much?” “What! Dana! That’s a lot of money to give away, can we even afford that?”

“Kathy, I’ve always gone over our monthly expenses as well as our annual tax returns with you. We- you, me, our company, just delivered a grand slam on our biggest project yet. Three C-level executives to revamp the manufacturing process for one of the largest companies in the world. Our fee was $1.5 million. I think we can afford it.”

I wondered what I said wrong when Kathy gave me this puzzled look and said: “Then why am I still working Dana?”

End of Part 4

Dana’s Story, Part 5

Why Is Kathy Working?

“That’s a valid question Kathy. I thought you worked because you like what you do. You always seem to be able to leave the office behind when you come home. If we could, Emily and I would love to have you at home with us all the time.”

“I do love working Dana, but for what you are paying these three, maybe I should shift to full-time homemaker.” Kathy made about the same amount as I paid each one of the three researchers.

“Nothing would please us more.” But also think about what you would be giving up. Maybe there is a way to cut back your hours or do your administrative work at home one day a week.” Even though what I said was true, there was a little part of me that didn’t want to give up the wife’s coffee club get-togethers and exercising with our little girls.

Hiring Cori, Laura, and Kim enabled me to keep up with my growing client demands. I was also able to further adjust my schedule to accommodate Emily’s growing needs. These three also became my very good friends and we frequent planned play dates, getting both our daughters and families together. I was excited to expand my support network to help my employees as we were frequently baby-sitting for each other.

Emily was now growing out of her ‘baby things into toddler. We started to change our play time to art class. We started out with Paper Mache flowers. It was very interesting to see how Emily reacted to colors and shapes. The colors would fascinate her for hours on end. She tired of the shapes quickly. I found it pretty amazing that colors could keep our little girl so fascinated. I thought if she liked colors, I would get her more colors! I found a lot of eye shadow pallets at our local dollar store. Emily and I had so much fun putting on eye shadows. Kathy would just laugh when she came home when we were knee deep in make-up.

Laura and I started to get together almost every day to take ‘Butterfly Consulting’ into overdrive. Kathy was very supportive and usually sat with Laura and I when she could. Kathy had insights into women’s styles and behaviors she learned from her corporate marketing people. Kathy thought if we could present a strong united woman’s front, then it was well past the time for women to take a seat at the table.

I was thrilled to be able to work with Laura to give women opportunities to enter positions that previously not been accessible to them.

More Good News

Kathy and I found out that we were expecting again, but there was a twist. There were two little girls living inside Kathy’s womb. Twins. For some reason, I was fascinated with having twins and couldn’t wait. Kathy got a bit moody after the initial morning sickness passed. I was concerned for her, but she didn’t want to talk about it. I didn’t know if it was work or the pregnancy or me or what? I asked one my neighbors, Beth to see if she could talk to Kathy.

I guess I wasn’t as perceptive as I thought. Kathy told Beth she was afraid of reoccurring issues with her pregnancy, especially the thought of having to breastfeed again. I was very proud of the way she wanted to keep pressing forward, but I knew we had a problem we had to solve together.

Kathy’s OBGYN, Dr. Cynthia Morris advised us at one our earliest pre-natal visits that she was recommending that this to be our last pregnancy. She was worried about Kathy’s mental and physical well-being and so was I. Having three kids, a spouse and a loving family was what we signed up for and I wanted to make sure Kathy was there to enjoy it too. However, now that our family was established and we weren’t going to have any more babies, it opened up a new door and opportunity for me. Not concerned about my sperm count anymore, I started taking Kathy’s birth control pills immediately, twice a day. Then I ordered a new six-month supply. Better to be safe than sorry, my parents always told me.

I was not looking forward to reliving Kathy’s breastfeeding nightmare either, so we needed to come up with a solution in the next 7 months. If it were up to me, I would give anything to be able to breastfeed our twins. There are obviously many, many alternatives to breastfeeding, and while a man breastfeeding wasn’t science fiction, it was damn close to it. If I really wanted to breastfeed, I needed a plan. I found one on the internet (it must be true if you read it on the internet) and now had hope! The next step for me was to enlist the help of my neighborhood wives club. I let it slip on several occasions that I would be more than happy to breastfeed, “if only that was possible.” Sigh.

Next up for the neighborhood wives club: water aerobics with the babies! We had now established a bit of a routine. Mondays we got together for coffee at 9, then craft time with the girls. It was really more a slumber party with the girls happy to play together. Tuesdays and Thursdays were mom and tot’s yoga. Now we were adding water aerobics Wednesday and Friday. But that’s what neighbors do. We all had built in pools and hot tubs. I think it’s called “keeping up with the Jones”.

Pools in the upper Midwest are a blessing and a curse. They are so fun in the summer to just jump in and cool off. But the pool season is very short, from Memorial Day to Labor Day. Just three short months of frolicking, but a load of work. It was a labor of love as the neighborhood men took advantage of the nice pre-Memorial Day weather to open up the pools. There were tarps to take off and hose down, debris to clean out and then we tried to navigate the chemicals.

I was finishing up checking our water condition on Sunday, relaxing with Kathy and Emily when Kathy noticed my breasts were bigger than normal. “Dana, what’s going on with your chest, err breasts?” Well, there was only one plausible explanation. “It must be from wearing the bras and camisoles all the time. I just love the way they feel, but they must be reshaping my body somehow?” I said this using the best poker face I could conjure up. “Wow, that must be it! But you can’t do water-aerobics with the other moms and tots like that. Your new breasts would be too confusing for everyone. Let me see what I can find at work tomorrow for you.” Oh really? A new bathing suit for Dana? Will Kathy find a me a one piece or bikinis to wear? I felt like a kid on Christmas eve, waiting for Kathy to come home and “surprise me.”

Kathy didn’t disappoint and I was now the proud owner of several new one-piece women’s bathing suits that were built for competitive swimmers and fit like a glove. She also thought it was cute for me to try a bikini as well, so she got me two. She also bought matching bathing suits for Emily and a few for herself, too. I tried my best to show my best pouty face. “What do you think the other ladies will say, Kathy? Should I call and warn them about my bathing suit for aerobics tomorrow?” Kathy took the proverbial bull by the horns: “if they don’t like it, they don’t need to come!” Well said, my protector. I will dutifully wear my new women’s bathing suits proudly.

The coffee club ladies didn’t miss a beat when we all took off our cover-ups and got our little girls into their cute suits and pool diapers. I felt like a porn star in my skin-tight suit with my nipples looking like high beam headlights on full display. “Is that a new suit Dana? It looks terrific on you!” Beth was practically gushing. “Kathy picked it up for me at Lord and Taylor yesterday. It’s so comfortable and she was able to get a matching suit for Emily.” I held up Emily next to me and we both gave her our best smiles. “We need to up our game girls, Beth exclaimed to Paula and Gabrielle.” Every time Kathy brings clothes home from work, Dana ends up looking like a Supermodel!” I loved these coffee club girls. The other wives always made me feel right at home and Emily had some wonderful playmates.

My new bathing suit was wonderful, but now that I had budding breasts, my nipples were on full display. As we finished the water aerobics and were getting dried off, my friends noticed my nipples were on high alert. As I was blushing, an idea popped into my head. I invited everyone in for some healthy snacks and drinks. We gave the girls juice boxes and toasty oats. The ladies all had coffee. As everyone settled in, in front of the other girls, I asked Beth if she would give me her opinion of something I found on the internet. Of course, all three wanted to see. We picked up our babies, who were getting a bit fussy and hungry. The perfect setting for… “Beth, look at this site. They are showing men breastfeeding their babies! How can that be possible? Do you think it’s some kind of hoax?” I had baited the hook, and now I was waiting for a bite… Patiently… Then finally!

“OMG Dana! Do you know what this could mean? You may have just solved Kathy’s deepest, darkest concern about this pregnancy. Would you really do that? We all have breastfed our babies but didn’t have the problems that Kathy experienced. You would be the best husband ever, although you are pretty high on the list right now.” The other women looked at me, then at the website, then at my boobs, then back to the site, then my hair and nails, then back to the site, then at my earrings, then back at the site. The looks of understanding and grins of excitement quickly spread on their faces.

“I don’t see what the problem is,” Gabrielle chimed in. “All I see is one of our favorite coffee moms about to make the most unbelievable sacrifice any man could for his wife!” Paula chimed in, “we are going to have to do some serious shopping ladies if we are going to have our little Dana properly outfitted.”

“Thanks for the support ladies, but there is one big hurdle here, actually two or three. First of all, “Is this even possible or just a hoax? Second, who is going to tell Kathy that her husband is going to nurse her twins? This need to be her idea. I’m totally on board but she needs to behind it 100%. And lastly, I really don’t have the boobs to feed twins, but I’ll do whatever is needed.” This indeed was a tricky one. I was at best an A cup, but I would need “full power” to satisfy two hungry babies at once. The ladies wanted to see my breasts, so I thought, heck, why not? They were oohing and aahing and all of them were very touchy with me until they were fully satisfied that I had indeed budded and was on my way. Next stop, C-cups or bust! (pun intended)

“Don’t you worry that little pretty head of yours Dana. We have the situation well in hand.” We headed out to VS and I experienced the next best day ever. Elena, our ‘Angel’ was delighted to help me get my pregnancy wardrobe started. I didn’t know there was ‘pregnancy’ everything. I now had panties, bras, nursing bras, belly belts, camisoles and a few naughty stockings thrown in for good measure.

I know what you’re thinking, that’s one step over the line, sweet Jesus. But I was in crossdressing heaven and my wife was my escort. Kathy was the expert in charge of my wardrobe, and there wasn’t a lot a space devoted to men’s clothing in my closet. She demanded I wear top of the line suits and accessories. St. John was my favorite. Although I think it makes me look older, with my clientele, looking older than my mid-20’s was a definite plus. When Kathy had perfected my look, I was comfortable in the board room or having power-lunches with my network of powerful women. Now that Samantha and Kathy had firmly declared “No more pantsuits” I was in pencil skirts and mid to high heels most days and loving it.

It’s a cliché for cross dressers, but my shoe collection was getting out of control. I even bought a pair of ballet boots that Kathy thought was just crazy. I actually worked myself up to be able to adequately walk around in them. The coffee club girls thought I was insane to even attempt walking in the boots, but I challenged them to give it a try. We had dinner with our families after that while wearing our ballet boots. I thought the husbands and Kathy were funny trying to goad us into a dance line with our ballet boots on. They were extremely sexy and the ‘girls’ filled me in on all their sexual exploits that night. That was another night I’ll never forget. When Beth and Kathy got together, there was some sort of sexual download that took place. When everyone had gone home and we put Emily to bed, I felt I was being ‘stalked’. Kathy was on horny overload for some reason, but I wasn’t complaining. We both gave each other a nipple workout and her vajayjay got a good oral workout from me as well.

Kathy and I worked out frequently, and lately she had been coming home with pretty packages for me and Emily. As Emily and I had fun tearing off the wrapping, I was secretly thrilled to see an all-in-one girdle! Kathy said they had some new designer suits coming in soon and wanted to make sure I would fit! My heart thought back to my younger years and my mom’s girdle. Had I come fully round the circle of life? A girdle for me? What am I, fat? Oh, I am getting the vapors, I will live in my new girdles.

I will admit that I couldn’t wait to try the girdle on with one of my outfits, but I thanked Kathy profusely and told her it would come in handy in my upcoming Friday meeting with another potential client. At this time, one of the researchers, Laura Hill, was inquiring whether she could take on more responsibilities. I was thrilled at her assertiveness and we proceeded to tag-team on several client visits as two professional women meeting dynamic female corporate execs. I asked Laura about this change for her, and how I could help? She said her time at home was freed up and she wanted to graduate from research to consultant. I was overjoyed. I had been searching for a partner that would enable me to again review and re-focus our business plan.

We talked a while about my appearance. “Laura, Kathy has me in women’s clothing every single day and I wonder how you view that?” Laura was like my best sister. “I think Dana looks much more professional in skirts than in those 80’s pantsuits! Woohoo, no more pantsuits is my mantra. Laura had a very compatible thought process to mine. We weren’t judgmental.

Laura was like a sponge and we spent a lot of time together working side by side so that she could learn what I did, too. We were able to add another researcher and Laura and I worked together on a lot of interesting projects. I don’t know if Kathy felt jealous, but she never mentioned anything to me. I had no romantic interest in Laura at all. I saw her like a sister and our little girls loved playing together too. I just got some funny vibes from Kathy that I could tell she was worried about me.

But boobs, big boobs? There is no going back from breastfeeding twins for 9 months to a year. In addition to requiring more volume (bigger boobs), I needed to get a grasp on feeding schedules, pumping, nipple care (Kathy’s nipples got cracked and infected and I was not going to repeat that craziness.) But I was getting mighty close to exactly what I had in mind. 24/7 dressing with both my wife and friends full support. And I get my own boobs!!!

End of Part 5

Dana’s Story, Part 6
Dana has been welcomed into the neighborhood wives club, now he enlists their help to achieve his next goal.

The Milk Train

The coffee club girls didn’t waste a minute getting me on the breastfeeding path to nutritional life. First of all, I was sent to visit my wife’s OBGYN all by myself. Dr. Cynthia Morris was a delightful D.O., graduating from my alma mater several years ahead of myself. She had a concerned look on her face when we sat in one of the patient rooms to talk. “I know you are worried about Kathy and I am too. I am going to monitor her closely to head off any problems.” “You are an angel, Doctor. I am concerned about Kathy and would do anything to make sure she is safe.” I then explained my concern about her breastfeeding and how it was taking a severe toll on Kathy’s psyche.

I then started pulling copies of the websites on men breastfeeding to show Dr. Morris. I again reiterated my desire do anything to alleviate this gnawing concern of Kathy’s. I even told the Doctor about the neighborhood wives coffee club and ‘their’ bold suggestions.

Dr. Morris looked at me like I was ET. “Do you realize what you’re asking? Are you really ready to commit to breastfeeding twins for the next year?” “My questions to you are: Doctor, is this a possibility? Would it work for us? What do we need to make this happen? How how big do my boobs need to be to supply enough nourishment for twin babies? Do you think this is a good idea? And if you agree, then lastly how should I approach this with Kathy?”

Again, I got a blank look from Doctor Morris. She hesitatingly said to me “it sounds like you’ve given this quite a bit of thought. Aside from the size of your breasts, do you have any other concerns?”

“I want to make sure that if I can lactate, that the milk will be nourishing and safe for the twins. I would also like to discuss long-term feeding schedules.” Dr. Morris was regaining her composure and I could see her brain start to begin working on solving the problem at hand “Would you disrobe so I can examine you? I’ll call another nurse to join us. Put on the gown on the table and I’ll be right back in.” Dr. Morris looked serious and I wondered if I had lost all hope in pulling this off. But…My first OBGYN exam! That’s another check mark on the bucket list.

The first person to enter my exam room was a young nurse whose nametag read: Julie. Julie was pleasant while she took my vitals as well as three vials of blood and a urine sample. Height, Weight, Good BMI, BP, Pulse, Temp; no problems. Dr. Morris entered the room and Julie took a seat. I was holding my breath, hoping my explanations would sway Dr. Morris to help. If she said no, my plan was dead in the water. I was so close to the finish line.

Please god, get me over the finish line, goal line or whatever line in the sand I need to cross.

The Exam

Dr. Morris came back in full professional mode. She started with my breasts. Her eyes got huge as she gave me a breast exam. “Dana, how long have you had breasts? “I’ve just noticed it over the past month or so. Kathy and I thought it was because of my wearing bras all the time under my suits.” “Dana, these are honest to goodness, beautiful, women’s burgeoning breasts. What size bra do you wear?” I think I’m currently a 34-A cup. Do you think they will be big enough to allow me to nurse our twins?” I thought nurse Julie’s head was going to explode listening to our conversation! Dr. Morris then proceeded to the bottom part of my body to examine. Another bucket check mark for feet in stirrups. Dr. Morris examined my “equipment” as Julie was intensely watching, Dr. Morris asked, “do you have any problems urinating? “No.” “How often do you have erections?” “Whenever I see my wife.” Good answer Dana!

I want to see you back here tomorrow morning so I can get the results of your blood and urine samples and we can determine a course of action” “Listen doctor, I know this is a lot to take in. But, please be honest with me. Is this just a pipe dream of mine to help Kathy or can it possibly work? Dr. Morris looked at me again like I was an alien. “If you are 100% committed and your bloodwork comes back ok, we can talk about next steps.” I was on pins and needles. Please lord, let the angels sing!

Now I had to address the task of how to break the news to Kathy. Ok, I’m really not going to do that right now, I’ll just lay a little foundation for the future. When Kathy got home, Emily and I were waiting there for her. “Kathy, you go get changed then you can come back to play with Emily before dinner.” “Yes, ma’am”, she saluted us before scampering off to the bedroom.

Dinner was great. I was constantly amazed at Kathy’s ability to leave all of her work behind and be in the moment with Emily and me. I worked up the courage to lay one more foundation stone. “Kathy, I followed up on your suggestion regarding my budding breasts and saw Dr. Morris today.” “Dana, you should have told me, I wanted to come to support you.” “I didn’t want to worry you and Dr. Morris just did some tests. She wants me to come back tomorrow to discuss the results. I’ll call you as soon as I’m done.”

Kathy was beside herself with worry, but I told her Dr. Morris said we can handle this.” However, the wives’ coffee club was not so laid back. “We are coming with you, like it or not Dana!” Beth explained to me. Ok, fine. This enabled Kathy to get Emily and I all dressed up so we could compete with our neighbors. Kathy was totally amused at my predicament and offered to lay out our clothes. “Thank you, I replied. That would be a tremendous help. I don’t want to commit some kind of mommy faux pas.

The Hard Truth

We looked like a ‘Wives of the Midwest’ entourage as we headed to Dr. Cynthia’s office. When ‘Dana’ was called, most of the waiting room got up with me. The nurse quickly realized we needed a bigger boat! Okay, not a bigger boat (hahaha), but definitely a bigger room. When Doctor Cynthia walked in, she saw four women, four baby girls, and one nurse. Instant bedlam.

“Okay, let’s get started. Why do we have so many people in here for a confidential medical discussion?” I started to explain when Beth spoke up “We are Dana and Kathy’s best friends and we want to help Dana breastfeed the twins when they are born. Can you help us?” I loved my coffee club girls. They were definitely no nonsense, and right to the point!

After I clearly signed, initialed and notated that I waived all privacy and HIPAA laws, Dr. Cynthia opened my folder and got started. “Dana, your testosterone levels are a little low, but your estrogen levels are through the roof. Can you explain this?” I said, “I’m not sure Doctor, but this is my conjecture. I have been immersed into a woman’s world with my wife, daughter and business. I think my brain may be trying to match my body with my heart.” A great answer! But I don’t think the good doctor was buying a word of it. “Doctor, does that also explain my ever-growing breasts, too?” I was going for a home run, but I’d settle for a base hit!

Dr. Cynthia (I like that much better than Dr. Morris) gave me a soul-searching stare and then smiled. “Dana, if you weren’t married, I would be down on one knee right now. This is the most selfless thing I’ve ever heard of. I would be honored to help you and Kathy. What just happened??? “I’m on the road again, going places that I’ve never been. Seeing things I may never see again. And I can’t wait to get on the road again.”

The neighbors started screaming, the babies started crying and I couldn’t believe my ears. Hallelujah! “Great, thank you! What’s the first step? And the second?” Dr. Cynthia explained that we need to increase the estrogen and progesterone levels in my body. I also needed to stop any excess testosterone production. I knew immediately what she meant. I was both terrified and excited beyond belief. She was telling me I needed an orchiectomy for this all to work, or a similar chemical castration. A few days prior to Kathy delivering the twins, I would get dosed with prolactin to let down my milk. I was trying my best not to panic or show my elation. Without my testes, life would be much easier for me. No uncomfortable tucking, no chance of Kathy getting pregnant again, and opening up my chance to breastfeed our new twins.

As I recovered my composure, the girls were all hugging me. Dr. Cynthia had a huge grin on her face. “I can’t believe we are doing this Dana. I am going to write a doctoral thesis paper on your journey, I am so proud to help you.” Okay, but when do I lose my balls?

We still had several steps before the boys got put down. Dr. Cynthia was adamant when she told us it was possible for me to breastfeed our girls. The other two questions needed closure as well. “How are we going to talk to Kathy about this? I know it weighs heavily on her mind daily. All of a sudden there was a gathering tornado as my Doctor and my good friends laid out their plans. “We are going to have a neighborhood BBQ this Saturday and we’ll do the rest with Kathy. Ok? That was easy enough. Next up: are my boobs big enough to take care of the twins?

Dr. Cynthia was very clinical in answering my last question about volume (boob size). “Dana, you have developed into an A cup on your own. That is probably not big enough for nursing twins, but you needn’t worry. With your body structure and your new hormone regimen, you’ll be a full C cup well before the twins are born. Those will be the perfect size for the twins. Tada! My own C cup breasts!

Now I thought my carefully laid plans were finally coming to fruition. I still had to take a deep breath to make sure I was ok with this one-way trip to womanhood. No more balls, big boobs (okay, only a C, but big for me!) Being a wet-nurse for the twins. It would be difficult to have any semblance of maleness after this. Was I ok with that? What are Emily and the twins going to call me? Dad? Mom? Auntie? Before the cart gets before the horse, Kathy had to be 100% on board with this or it still doesn’t work for me.

We thanked the good Doctor and left. I rode back home partially in a daze. Would this really work?

Saturday finally arrived and we got ready to get together with the neighbors. Kathy had a late night at work, so I got Emily up and took care of her needs. Emily and I made breakfast for Kathy and put together a tray to take to her in bed. I think the smell of fresh coffee woke her up, but she was all smiles with Emily and I bringing her breakfast in bed. I gave Emily to Kathy and then proceeded to feed her while she played with Emily. It was a memory I would treasure.

I knew Kathy’s decision was coming today, but I had a real trepidation that I should stop this runaway train before it crashes. I took Emily and got us both dressed. Emily was in a cute princess dress and I was wearing tan shorts with a sleeveless polo with tan sandals. Kathy met us in the kitchen wearing a cute pair of capris with baby animals all over. She had a crop-top on that showed off her tight body, even with her tiny mommy belly. She was nearing the end of her first trimester.

We headed over to Beth’s house for the BBQ today. We brought our bathing suits and plenty of diapers and supplies for Emily. I had made a fruit salad to bring, so we packed it all up in our wagon with our little girl and headed off. The weather was fine, and the food and company were great. Dr. Cynthia showed up with Vicky and we all doted on our little ones.

The moment of truth was at hand, and I was getting sick to my stomach. Finally, we finished eating and we were just getting ready to gather everything up and head back home when my coffee club friends, along with Dr. Cynthia had a private moment with Kathy. I wanted to grab Emily and run, but I dutifully sat there entertaining our little girl and her friends while the adults (women) talked. I started to get some weird vibes from the group. There were a couple of thumbs up and smiles, but never any discernable expression from my wife.

Kathy walked over to us and started sobbing. “You sweet, sweet, wonderful husband. What did I do to deserve you?”

“You know I have always told you I would do whatever it takes for you and Emily. We want you to be safe and happy.”

End of Part 6

Dana’s Story, Part 7
Next steps for Dana with the coffee club and work. Can Dr. Cynthia help?

New Beginnings

That day would prove to be pivotal in our life. The coffee club was totally excited. That night when we finally went to the bedroom, Kathy was revved up and raring to go. We were careful of her belly, but we fell asleep after thoroughly exhausting each other. I woke up only minutes later for my night feeding with Emily. There wouldn’t be many more of those.

Monday morning, Kathy and I were at Dr. Cynthia’s office. This time we dressed almost identically with sundresses and sandals. After the BBQ, Kathy had become much more touchy-feely with Emily, which we both adored. That morning, I showered, then got Emily dressed and fed while Kathy got ready. Kathy laid out my outfit, which was identical to hers and Emily’s. I dutifully put on matching baby blue panties and bra. She couldn’t keep her hands off my little boobs, adjusting until they were just right. She handed me a pair of nude pantyhose and then slipped the dress over me and zipped me up. It was so sensual. I didn’t know if we were going to make it out of there. I marveled at the change in attitude from the first Halloween to my current way of dressing. Then she sat me down and re-did my make-up exactly like hers. What fun.

Dr. Cynthia had a big grin when she greeted us. Her nurse took both of our vitals. Then she collected blood and urine as well. Dr. Cynthia asked me to get undressed and put on the gown and left the room for a few minutes. Kathy was holding Emily while watching me with hungry eyes. I put the gown on and was standing there when Dr. Cynthia knocked and came in and asked me to sit in the exam chair, with her nurse by her side. She went over both our charts and started with Kathy. “Your health is excellent Kathy, but we need to monitor you closely.” We looked at each and smiled.

“Now we come to Miss Dana! Kathy, come over here so you can see exactly what we are working with.” She put my feet in the stirrups and had me lean back. “You can see here Kathy where his equipment is, we wouldn’t change much, just something to ensure no more pregnancies for you and to eliminate testosterone from interfering with her breasts.” Then she moved up to my breasts, with Kathy bending over me closely on the other side of me. “Can you feel his breasts, Kathy, like you were doing a self-exam? She led Kathy through a thorough examination of my new breasts. Can you actually feel the breast tissue underneath? For some unknown reason Dana has exquisite, womanly breasts and I think he can possibly nurse your babies!” At that moment, Emily decided to come to me, but immediately grabbed my boob. “Whoa, that feels a little different.” Dr. Cynthia said that infants could smell the milk, which helped draw them in.

I felt somewhat awkward sitting there in an exam chair holding Emily who was holding my boob. That’s when Dr. Cynthia took Kathy over to sit down for ‘the talk’. “It’s time to talk about what would happen if we move forward. For some reason, Dana has breasts and could possibly feed the twins. In order to do that, we would need to start several things. We need to pump up his estrogen levels and reduce his testosterone levels quickly so he can develop enough volume to adequately feed two hungry babies. A few days before your delivery date, we will induce lactation in him and then nature will take over. He should have plenty of milk, quite nourishing for the newborns.”

“Any questions?” she said with a chuckle.

Kathy looked at me and said, “I don’t understand everything, but I don’t know how to thank you.”

I started us out, “I have to know something Kathy. We’ve gone through a lot together, but this will mean some big changes for me as well. I’m more than willing, but I have to know that you are behind this 100% with no reservations.” She came over and gave me a big kiss. “Of course, I am. You are my soulmate!”

Kathy turned to Dr. Cyn. “Just three more questions Doctor: Will his boobs be bigger than mine?” hahaha Will his friend between his legs get larger or smaller?” And lastly, will our friend stop working?

Will ‘it’ Stop working?

Dr. Cynthia was ready, God bless her heart. “That’s what we need to discuss here: Everyone’s reproductive health. Kathy let’s start with you first. What are we going to do with you after the birth? I have recommended that we eliminate the possibility of future pregnancies, but I wouldn’t recommend a hysterectomy to a healthy woman like you. Let’s take a look at you after delivery, there’s no rush.”

Now, another decision needed to be made. But this one couldn’t wait a minute longer. We had two choices to get my body onboard the nursing train. They both concerned my boys hanging below the belt. Do I want to take anti-androgens to kill off my testosterone production? Or should I just give the boys a one-time sendoff? The latter sounded like the best option for me and I’d also get a sleek look down below.

This was a huge step for me. I didn’t start cross-dressing with the idea of a full SRT as my end goal. I liked the idea of our nuclear family and wondered about my role. Would I still be Daddy, or will I become a second mom, or aunt, or cousin, or just ‘Dana.’ Whatever I’m called, I’m going to have a woman’s body and outstanding décolletage.

Then Dr. Cyn turned to me. “Okay little mommy, time to make a decision, scalpel or pills? We need to eliminate most of the testosterone in your system to let your breasts develop fully. Depending on your decision, we will also need to plan on HRT for you.”

“Doctor, I have done a lot of research and soul-searching on this and my thought is the orchiectomy has less side effects than taking anti-androgen pills, considering the quality of the milk for the twins.”

“That would be my recommendation also. But I can give no promises and how your penis will work.”

I looked at Kathy, “are you ready?” She gave me another kiss! “Let’s get you started little mommy. I love you so much.”

The Journey Begins Anew

Dr. Cynthia’s nurse came back and soon Kathy and I were both signing documents for me to get my boys lopped off and my boobs going! We were sent to the medical building next door after I got dressed. I was taken to an exam room and asked to undress again. The nurse was very chatty and took my vitals again, drew more blood, and I gave another urine sample. Then I got into another exam chair with stirrups. Kathy, Emily and I were a bit startled when a tall, very striking middle-aged woman came in that had ‘Dr. Sullivan’ embroidered over her left breast.

She introduced herself and was looking at me very carefully. “Do you know why we are here today, Dana?” “Yes, my boys have done their job, now they need to take a long walk off a short pier.” She chuckled at my joke and looked at Kathy who was looking back with loving eyes. “And this is ok with you, Kathy?” “Oh, yes Doctor. I’ve married the most wonderful man in the world. I had real trouble with my last pregnancy, so Dr. Morris said this should be the last for me. And now we have twins on the way and Dana is going to nurse them”

Doctor Sullivan’s eyes got wide as she looked back at me. “Let’s do a quick exam then we can talk. Dr. Sullivan pulled back my gown and took a close look at my manly parts. I was a little twitchy as she handled them for inspection. My ‘guy’ took this time to show how proud he could be. “I’m sorry, Doctor. It has a mind of its own.” “Well everything seems to be healthy down below. Tell me again why you are saying sayonara to your testes?” I proceeded to tell her the story about Kathy’s breastfeeding problems and the ‘discovery’ by the coffee club. The doctor gave me another weird look and proceeded to the top half of my exam. She began her exam of my breasts and was giving them a thorough kneading. “Well, well, well. Now I can see the interest in breastfeeding. But your breasts aren’t large enough to nurse twins, so you want to get rid of your testes and fill your body with estrogen so they will grow. Is that about it?”

It sounded so simple when she said it. I’m donating my balls and growing breasts to help my wife. “You’ve got it Doc. When can we get started? I just want to make sure you know I don’t want anything else done to old Danaboy down there. “Are you sure?” she said. We could just turn it inside out, inside you.” She laughed and winked as I covered up my groin with my hands.

“We just have to wait for your bloodwork to come back, but I’ll send the nurse in to get you ready. One other item I would highly recommend. Even though you are not planning any more pregnancies, I would still preserve a semen sample. What? When? Where? Right now?

“We’ll give you a few minutes. There is a cryogenic-ready tube on the counter. As the Doc was leaving, Kathy put Emily on my chest as she was getting fussy. I took a deep sign as she laid her head down on me. I nearly jumped out of the chair when Kathy grabbed my penis and gave it a kiss. “This little guy has been terrific for me, let me take care of this for you.” I was trying my best to hold Emily still, when she reached out and grabbed my boob. She laid her head back down on my chest with a firm grasp on my left boob. That scene was etched in my mind and I would fondly recall our little family in that exam room. I had Emily snoozing on my chest, firmly grasping my little boob, while my wife was dutifully extracting a sperm sample. It was a full sample.

After that, I really didn’t even need anesthesia. But Nurse Sandy came in and got me prepped with an IV drip. The rest was a blur and was over quickly. Dr. Sullivan saw me as I was regaining consciousness in the recovery room. She handed Kathy a little jar with my testes swimming in formaldehyde. “A little souvenir for you Dana. I’ve been told they can be made into earrings or a necklace for you.” Hahaha Those two little blobs were now officially off ‘Team Dana’ and I didn’t need any reminder.

Dr. Cynthia came in while Dr. Sullivan was leaving. “How are our two little mommies feeling? Kathy grabbed her in a big hug. “Oh, thank you doctor! I can’t tell you what total relief this has been to resolve my past breastfeeding issues. I am so excited about the twins and the past is totally in the rear-view mirror.” Dr. Cyn leaned over and whispered to me, “Are you ready to ‘Release the Kraken?’ I was really beginning to like Dr. Cyn. Her nurse showed up with several syringes on a tray. Is this room service? Do I pick one from column A and one from column B? I am ready to have my estrogen friends running free!

My frivolity was cut short when I was told to bend over and assume the position. There isn’t much humor in getting syringes emptied in my two well-toned buttocks. The first was an anti-androgen to cleanse my body of any leftover testosterone. The second was a female estrogen, with other stuff in a concoction to try to convince my body that I’m pregnant and need bigger boobs. The last item was inserted subcutaneously a few inches below my belly button. This was the mack-daddy. I now had a time release estrogen capsule in my belly and there was no going back. Not that I wanted to go back to anything. I loved my wife, our daughter Emily, and I was now going full-time as feminine Dana.

We left the medical building and were finally headed home. I was feeling a bit strange. I had a dull ache to remind me the boys were swimming with the fishes. Dr. Cyn told me to expect some craziness for a few days with the hormones. I got Emily out of her car seat and we all walked back in. It was about dinner time and I thought I had better get started. I sat Emily down in her highchair with a sippy cup and cereal on her tray. No sooner than I turned around to start dinner, the doorbell rang. The coffee club wives, with husbands in tow carrying food and drink came rushing through. We were all hugging and crying about the good news. The guys at least got the food out of the take-out containers so we could eat. I sat there on the floor in the midst of a gaggle of little girls. I was so thankful. I was so excited I couldn’t eat much.

That was a godsend because when I got up with Emily in the morning I had to hurry off to the bathroom first. That’s where Kathy found me clutching the commode. She came over and held my hair back while wiping my face off with a washcloth. “My poor baby. You have morning sickness because of the hormones.” Kathy helped me to the kitchen table and came back a few minutes later with Emily. “My little nurse needs her strength.” I couldn’t even look at Emily’s baby food without retching, but I found toast and coffee helped my stomach calm down. The nausea only lasted a couple of weeks, but it did help me to lose a little more weight around my waist.

We did have some turnover in our little neighborhood. Paula and Adam moved to Germany. Adam was thrilled about working for the top German automaker. Paula was eager to immerse her daughter Julianna in another culture. At the same time my friend Samantha and her partner Vicky moved into the upscale house next to ours. I was so happy with the support group I had and was overjoyed for the friendship of Samantha and Vicky. Janice and Joseph Stephens moved into the house Paula and Adam left, and guess what? She was pregnant and due around the time of Kathy. This neighborhood had a real problem with wanted pregnancies.

End of Part 7

Dana’s Story, Part 8

Dana and Kathy prepare for the upcoming birth of their twins. Dana has a few challenges to be able to take over feeding the twins after they are born.

Kathy and I went together to her pre-natal doctor visits, as well as La Maze and La Leche classes. We went to La Maze even though Dr. Cyn told us there was a good chance Kathy would have a Cesarean birth. I’ve never seen Kathy so excited as she was at our La Leche meetings. She had to show me how to do everything right to avoid the situation she had. My boobs were now overfilling a B cup and Kathy was pulling and prodding them to show me how to properly breast feed. At one of our last La Maze classes, when our instructor Cindy understood what was going on with us, she had a suggestion. “Dana, since your breasts are growing in anticipation of the delivery, I have a wonderful idea for you. One of the business’ a couple of doors down has a service that can outfit expecting fathers with a pregnancy belly so they can experience all the fun, too.” Kathy latched on to that idea and we were off again. I could end up with a realistic latex belly that could also be adjusted for volume. “Volume?” Our personnel shopper told me that Kathy and I would be nearly identical in body size with the new belly. “You can go in each week Dana and get filled up to match Kathy.” Kathy was ecstatic that we could be matching momma’s and immediately said we had a big shopping day ahead of us tomorrow at L&T.

I helped Kathy get ready in the morning after feeding Emily. I loved helping her get dressed. Kathy was really focusing on my nails for some reason. “Dana, your nails are so long, what are you going to do with them? Our plan was to let Emily spend quality time with Grandma while we staked out the mall. Kathy had on white lingerie, paired with white pants and a white linen tunic. That was certainly high profile. On the other hand, I looked like a soccer mom. I had my hair up high, short capris on with a long, multi-color tunic. Kathy put her arm around me and led me to The Salon and back to Paula. “Paula is going to help change all of this”, she said as she waved her hands around me.

At this point, having long ballerina nails and hair down near my waist, I was ready to keep going. Kathy asked me if I had any hesitation. Are you kidding me? Full speed ahead Captain, the dilithium crystals are holding together! “Yes, that sounds wonderful! Thank you!”

After Kathy left, Olivia and I walked back to her room. The waxing was exquisite, even around my bottom. She did give me a glass of wine to get started, which helped. Olivia noticed I was missing my boys, so I told her the short version that put me on the milking trail. She was squealing and had to inspect closely. Next, she made sure my new ‘girls’ got lots of attention. Olivia said I was her favorite customer. She said I was the only person she knew that loved getting waxed.

I was so relaxed after the wine and waxing, I just nodded as Paula was getting started. I told her I didn’t want too much cut off, but besides that, anything was fair game. After a shampoo and condition, I was taken to her chair. She started snipping just a little bit all over. Then she put in the highlights. I couldn’t really see what was going on when Leann pulled her cart over to me.

I hugged Leann and she took a look at my hands. “Wow, sweetie, your nails are getting really long, do you want me to cut them back. Even though they made my life a bit difficult, I really, really liked my long nails and asked if she had any suggestions. Did she ever! I ended with beautiful Stiletto nails and also a stunning henna tattoo that reached around from my thumb up to the tip of my first finger.

I was delighted with my nails and gave Leann another big hug. I couldn’t wait to see Kathy’s reaction.

After Paula finished my hair, it looked beautiful. My light brown hair now had blond and gold highlights and my hair was one big mass of curls.

As Maxine was finishing up my make-up, Kathy walked in with a long shopping bag she hung up for me. Maxine and Paula rushed in front of me and told Kathy she had to wait to see the finished product. They hustled me to the back and helped me into the dress Kathy had brought. It was a beautiful pink and lace creation. It had a form-fitting look from the low-cut top, down to the tight fit that ended just at my knee. She gave me silver stiletto heels and matching purse to go with the dress and we were done!

Kathy couldn’t believe the difference. My male self was now on a total vacation. She laughed when she saw my nails. “There’s no way you’ll be able to work with those!” Where there’s a will, there’s a way dear. She grabbed my arm and we drove over to the prosthetics shop near our Lamaze classes we were told to go see. The proprietor, Susan, greeted us and invited us to have a seat on the couch in her lobby. Her Transformation salon was very comfortable.

“What can I do for you two lovely ladies?” Kathy jumped right in with an abbreviated version of my volunteering to take over milking duties, as Sandy’s eyes got wide. “So, you’re here because your husband is going to nurse the twins you are carrying, and you want his body to simulate yours throughout the rest of your pregnancy? You’ve come to the right place! Once again, I needed to strip down so Sandy could measure me. Kathy ‘helped’ me get naked and I was shown to stand on a spot with two individual foot outlines on the floor. I was then given special dark skinny goggles like you use for suntanning and was told to hold my arms out to my sides and be very still. Sandy and Kathy pulled my guy back and taped me so I would have a smooth front. Then I heard the two of them moving back and machinery starting up. Sandy had a precise laser measuring system that soon had all of my vitals on a printout.

We came back a few days later for the fitting. Sandy explained the process. “We’ve made a skin-tone matching, latex type of prosthetic for you Dana. We will fit it to your body and then our laser measuring device activates the material to hold it to your skin. It’s quite remarkable to be able to wear. Your skin will still be able to breathe, and the belly has certain emollients to keep your skin soft. You’ll feel everything that Kathy feels from her back pain to her bladder pressure. We will even be able to have two ‘simulated’ babies swimming around in your belly so you can see how you need to adjust sometimes. You’ll come back every week after Kathy’s natal visits and let us know how much additional ballast to add. At full term, you’ll come back and we will reverse the process.” Sandy and Kathy were whispering and giggling while I was a bit uncomfortable. I would find out later about Kathy’s plans.

As simple as that seemed, I was now committed for the next five months. Kathy was so excited she got us both matching maternity dresses with stylish, kitten heels. “No more stilettos for you, missy! I would dearly miss my heels for the next few months.

Kathy handed Emily to me in a very similar style dress as ours, and we headed out for lunch. I had come a long, long way from just a few weeks ago. We looked like two pregnant moms out with our child. “I have to sit down Kathy, my back is killing me!” Kathy was laughing so hard she got the hiccups. It served her right. We had a light lunch and as we were finishing up, I got a sudden urge to pee so bad I thought I was going to wet my panties. Kathy started laughing again and pointed me to the lady’s room. I waddled in and did my business. Not much came out but what a relief! As I walked back to the table, I saw a smirking Kathy telling Emily that ‘Dana’ had to go wee-wee. That was only the beginning. I was constantly on the lookout for restrooms when we were out and about with Emily.

Kathy and I discussed at length that she wanted to cut back her work hours during her pregnancy. Her bosses at L&T were very pleased with her work and were more than happy to accommodate her wishes.

On Monday, we were all up and around and ready for our coffee club. Kathy fit right in with the girls. We were getting quite a group together. Of course, the first order of business was for me to strip once more so our friends could examine me. Does it hurt? Only when I’m not laying on my bed. Are your boobs bigger? I was approaching a full C cup status and the consensus was that we needed to go shopping for bigger, nursing bras for Dana. How big will the belly get? I looked at Kathy. “We now have matching bellies. As large as Kathy gets, I’ll get. It’s a good thing my boobs keep growing to match the rest of my body!

At our weekly OBGYN visit, Dr. Cyn was focused on my breasts. She said to Kathy, “Dana’s nipples need to be larger to accommodate the amount of milk flow needed. We don’t want a repeat of what happened with Emily.” Kathy was very supportive and wanted to get my nipples ready. “What can we do?” Dr. Cyn had a two-fold solution.1st, she wanted Kathy to manipulate my nipples whenever possible to stimulate more lactiferous ducts and increase the amount of milk production. Secondly, she wanted my nipples to get a little ‘tougher’ to handle two nursing infants at once. For that she suggested getting a breast pump to plump up my nipples.

It was hard to concentrate the next few days. Kathy sucked and sucked on my nipples in our bed. I was also on a daily ‘pumping routine’. The breast pump didn’t actually elicit any milk, but it automatically brought my nipples to ‘full attention’ when the pump was turned on. It was a good experience for the near future when I would be breastfeeding and pumping around the clock.

The next chapter in my life was starting to unfold. Next up was the Thanksgiving and Christmas Holidays. We were obviously going to have to go see both sets of the families with our double trouble. In the meantime, having Kathy around helped me immensely to catch up with Laura and our business.

End of Part 8

Dana is closing in on her ultimate dressing up goal. She just has a few more hurdles to get by.

Laura set up several client meeting, highlighting our unique capabilities. There was something funny going on about our new meetings. We made several new networking friends. But they were all focused on my ‘pregnancy.’ Denise wanted to know where I got my maternity dresses. She asked about when I started transitioning from my pre-pregnancy wardrobe? She actually asked to take a look at my nursing bras. I think my ‘pregnancy’ is going to be very bountiful for our company. Laura was thrilled with all of the business we were generating. At our next meeting, Laura surprised me. “Dana, I know you’re a man, but your ‘pregnancy’ has been awesome. I think I should know the experience to be ‘in the family way’ to sympathize like you do with our clients.”

I told Laura that my boys were swimming with the fishes, so I couldn’t help her there. Hahaha She laughed and said, “Dana, you are my idol. I have a partner and we want to have children, too.

I thought to myself, keep this compartmentalized. I needed to take this just one day at a time. The next day was water aerobics with the coffee club wives. We now were up to six moms and five tots. Kathy was adamant we had top of the line maternity swimsuits. She was busy and for my first day, I had on a one-piece with an orange top attached to a navy-blue bottom with a white sash between them. Kathy also wore a green one-piece maternity suit but hers had ruffles on the top half. My belly was now significant, so our water aerobics was a wonderful relief for me. Emily loved playing in the water with Kathy and me. My ‘belly’ was so buoyant I could float easily.

After we were dried, Beth spoke up, “The annual Halloween Party is at my house, we need a theme!” Kathy jumped right in, “Let’s do a Disney Princess Theme, all of the men can be woodsmen or princes, while the women will be Princesses. All of the girls where jumping and squealing. Kathy was jumping with joy. “I have the perfect costumes for us. We are going as Sleeping Beauty. Kathy said she would be the Prince and I would be Sleeping Beauty and Emily would be a Dwarf. Everyone was talking about costumes and decorations.

I was now little more than just meandering down the path of femininity. Kathy just claimed the male role in our Halloween without even a thought. I felt that this was actually an extremely important moment in my journey. Should I try to feign outrage? That would be silly. Should I try to retain some semblance of the alpha? That hadn’t worked so far. I wanted to confirm to Kathy that our family was secure, despite the changing roles. “Kathy, would you rather that I be the prince for Halloween?” “Why would I want that, Dana? You’ll make a beautiful Snow White.” “But Kathy, you are the woman in our relationship, you would make a wondrous Snow White, I replied. “Dana, things have changed with us. I feel more in charge than I was before. Is that weird?” “No, that is wonderful! I’m so glad you are taking control of your life. You are amazing. I’m happy to be Snow White, if that is what you wish.” “It is, Dana. I love being in charge. It’s probably just hormonal issues with my pregnancy, right?”

The next day was our weekly OBGYN visit. I held Emily as Kathy was going through her results with the Doctor. “You are doing great, Kathy. Your weight is on target and your vitals are in the right ranges.” Then she looked at me and said, “Now you missy, are a completely different story! Your estrogen levels are high. Your breasts are now almost a full C. You are well on your way to womanhood.” There were smiles and hugs all around. Kathy and I got up to leave and she said, “I’ll drive missy!” The next thing I knew, we were back at the Gurlz Salon. “Hi Paula,” my wife said. Dana is back for ‘The Works”!

Over the past several weeks, I had been managing to keep one or two vestiges of manhood. I know that sounds silly because of the nursing trail I’m pursuing. But now those were going to be ripped away as well. Paula told me that she was giving me the perm I requested along with a trim and eyebrow arch. She started by giving my hair a thorough conditioning and a light coloring rinse. As we walked over to her station, Paula pulled me close and said, ‘Don’t worry Dana, this will work out fabulously.’ I was terrified and thrilled at the same time. OMG, could I handle any more of this? Paula proceeded to roll all of my hair in a series of different sized curlers on my head then added the solution.

Paula then took me over to the hair dryers and started one up for me and set the timer. Then Leann sat down in front of me and we gave each other an air hug. “Dana, it’s so nice to see you. Let me look at your nails. You are a good girl Dana, no breaks! Today we can taper them into a longer stiletto profile and backfill by your cuticles.” I really enjoyed my time with Leann. It is a very sensual feeling getting the tips of your fingers worked over in the right environment. After this I could tell that there was no going back. I was now Ms. Dana 24/7.

When the dryer chimed off, I still had a few more steps. I had the neutralizing solution applied to my hair, then that was rinsed out and my hair was rolled again into bigger rollers. Then I was back under the hair dryer, then my hair was finally ‘done’.

I was done, Paula took me back to give me my ‘blow out’. Wow, how do I keep looking more and more feminine? Kathy came back and gave me an excited greeting. “You keep looking better and better, Dana. Motherhood certainly suits you!” I turned to Paula and whispered, “is all of this too much?” She pulled me close and said “Kathy wants the two of you looking like twins when the twins are born. Are you onboard with that?” “Absolutely onboard. Full Steam Ahead! I am behind my wife 100%.”

Paula asked me to come back in soon so she could show me some updo styles that would be easy for me. We agreed that I would come back Tuesday morning for my first lesson. Kathy was over the moon with my new perm and nails. We were getting closer to our due date and Kathy was taking control of our marriage. “Dana, I told Paula I want us to look like sisters when I deliver, do you like the results?” I loved the look and thought it would make things easier for us if we looked like sisters. “Kathy, I need to lose some weight for us to look more similar.” That sounded good to her, she decided I needed more liquids and less carbs and a more aggressive workout. Judging from her pre-pregnancy look, I needed some help to catch up. Kathy decided that I would start every day with Emily doing water aerobics!

I was no longer in crossdressing heaven. I had crossed over to the other side. My wife was in charge and I was now her wife! I was a motivated passenger on the approaching milk train, but I was still a little bit apprehensive.

Kathy was excited to go back to the Gurlz Salon for me to get started on my hair lessons. Tuesday morning, Kathy and I ready and set off for the salon with Emily. Kathy was very interested in Paula’s lessons, but wanted to make sure I was taking care of Emily at the same time. It was quite the distraction. I was able to put Emily in the carrier on my chest while Paula was giving me instructions. Emily was fascinated and started playing with my breasts while I was working on my hair. I loved the updo work that Paula showed me and knew it would be a tremendous help to keep my hair out of the way while nursing.

Kathy was in her nesting mode and we started cleaning and organizing everything in our house. Kathy had aprons for each of us as we worked together around the house. Beth, Paula and Gabrielle were frequent visitors and they were very interested in my nipple routines. Along with Kathy, they made sure I was using the breast pump frequently. I never was so involved with our neighbors. It seemed like all of the ladies, including Kathy wanted to help me ‘toughen’ up my nipples and even suggested having her daughter suck on my nipples to help me get used to the sensations. The first time she had Anna latch on to my nipple, I had an emotional release wash over me as I tried to relax. I felt like a mother when Anna latched on to my nipple and Kathy was right there guiding her mouth.

Halloween was rapidly approaching so Kathy got us appointments for our hair and nails. Paula put my hair in an updo and told Leann to do something special with my nails. She had a special color changing pigment that looked different in different lighting situations. Leann kept them long for me but warned me that nursing with extremely long nails could be a challenge.

Kathy got our costumes together and was excited about me being Snow White. I actually had Paula put my hair into a princess look and incorporated a tiara in my hair. Kathy helped me get my princess dress on without destroying my hair and makeup. After I was done, I helped Kathy into her ‘Prince Charming’ outfit. It looked more like a harem girl costume and when we were done, Kathy and Emily were ready to go. I figured it was time to get into character, so I was channeling my best Snow White when Kathy got out my ballet boots! She said I needed a little extra height and thought they would work well. I loved my ballet boots, but they are extremely difficult to wear for any length of time. I was thrilled. My wife had me fully dressed and trussed up and Emily was clinging to me.

I had to take a deep breath as we headed off to our neighbor’s party. By this time, all of the men just lumped me in with the women. I had no problem with that as I was more interested in chatting with the women, rather than the men. Beth had Anna with her, but Anna kept looking at me hungrily, and reaching out her hands to me. Beth had to laugh with her baby wanting to suckle my breast. Halloween that year made up for the one before. Kathy was 100% on board and she felt a sense of contentment knowing that I would be the one breastfeeding. “Dana, you need to get in better shape if you are going to be chasing three babies around.” Kathy took over complete control of my exercise regimen and I was able to lose another 10 lbs before delivery. The estrogen regimen was diligently moving my fat around and my waist was getting thinner, and my hips bigger, even though my belly prosthetic didn’t show it. My boobs had reached a real full C-cup and I was loving the feeling. Kathy kept working my nipples over to toughen them up. OMG, I think I love my nipples more than the thing between my thighs.

As we approached Thanksgiving, Kathy was at the forefront telling both our parents about my ‘sacrifice’ and warning them about our appearance. First we went to Kathy’s parents on Thanksgiving around noon. Kathy was immediately pulled into the kitchen to help finish with the preparations. She brought me and Emily along and soon we were cutting up vegetables and peeling potatoes for the meal. Kathy’s mom Nancy wanted to know about everything. She soon had me pulling my dress down so she could inspect my boobs. I was quite surprised when she started manipulating my nipples. “Dana, your nipples have grown so much. Your areola is the same size as Kathy’s, and it has also darkened in. You and Kathy are like twins!” Much to my surprise, Nancy was super supportive and was thrilled that her daughter didn’t have to go through the breastfeeding nightmare again. She wanted to look at my ‘belly’ and was amazed at the identical look for us both. ‘Dana, you are the most supportive husband I’ve ever heard of. You have taken a big worry off of Kathy.” I was now totally accepted to Nancy as her daughter’s wife and wet nurse. My boobs were indistinguishable from any woman and Nancy was thrilled that her daughter and grandchildren have a new source of breastmilk.

We then headed over to my parents in the afternoon. My parent’s, Bob and Phyllis, were quite apprehensive about my appearance. Phyllis took me aside when we came in. “Dana, why do you look like a duplicate of Kathy?” “Mom, I am trying to help Kathy with our twins, we want to breastfeed, but Kathy can’t do it.” “Why are your breasts so large Dana? Yours and mine look similar.” “Mom, I have been taking hormones to enlarge my breasts and when Kathy delivers, they will induce lactation. I think this will work out for our family. I really need your support, especially when the twins are born.” I was really hoping for support from my mom. She was my hero growing up and she always seemed to know just what to do. I was getting a little apprehensive about my rapidly approaching lactation and I wanted my mom firmly on my side. My mom wanted to exam my breasts and we had a nice mother/daughter moment. She took off her bra also and showed me how she breastfed us. I was amazed, but apparently women like to show and feel. Like Kathy and Nancy, she soon jumped on the Team Dana bandwagon with both feet and we kept moving down the milking trail.

We were now approaching two months before delivery. Doctor Cyn felt the best course of action for Kathy was a cesarean section. We were then able to schedule the delivery date and could start preparations. Since Kathy and I were spending so much time together now, it was more like living with my sister. We were still able to work in some cuddling and sex, but with both of us looking bigger than a house, our lovemaking was more sedate and lesbian like. I loved the cuddling with Kathy. We now had almost identical breasts and took advantage of that for both of us.

Christmas was on the horizon, so Kathy and I had several shopping excursions to buy presents for the neighbors, our doctors, our parents, each other and Emily. It was our best Christmas even though Kathy and I looked like we were going to burst. Beth and the coffee club girls were excited that our delivery was now less than a month away. We decided to do a gift exchange and I drew Gabrielle’s name. I think all of the girls were in agreement that we would get sexy lingerie for each other (so our husbands could rip them off us.

The holiday season was typically a slow time for business. Laura and I took advantage to go out and visit our clients. Now that I was full-term, it became more and more difficult for me to get around. Kathy delighted in getting me into my pregnancy dresses and helping me get ready for my meetings. As before, the women we met with were effusive in their praise for me. I could sense a big year coming up for Butterfly Consulting.

In the last week prior to delivery, Kathy and I were busy getting everything just right. When we next saw Dr. Cyn, she said it was time for my milk to come in. I got a shot of prolactin and by the next day, I was starting to leak. We got a chance to try out our breast pump for real this time and it worked just fine. After throwing out the first couple of bottles, we started to pump and freeze my milk. Beth brought Anna over for a trial run on my boobs, and other than being a little sore, I seemed to be doing fine. Mom called and said she was coming to stay for a while. Then Kathy’s mom said she coming to stay, too. We had quite the entourage when we took Kathy to the hospital.

The day before we were scheduled for delivery, Kathy and I went to see Sandy at Transformations to get my belly reversed. Sandy was delighted to see us again and told us about the reverse procedure. “Dana, women don’t go from pregnancy weight to normal in one day!” Today, we will drain about 90% of your water weight and will take the two simulation ‘babies’ out of your belly. If you exercise with Kathy over the next month, we will then take the ‘belly’ completely off you. Hallelujah! My belly was bumping into everything. I couldn’t wait to see it gone.

Finally, it was delivery day. Kathy didn’t experience the end of pregnancy issues she had with Emily, and we were both glad of that. It was refreshing to see how calm Kathy stayed the last two weeks. When our mothers showed up, it was like a camping trip with them. They immediately staked out their own bedrooms and started unpacking. When Emily was born, I was pretty much the sole caregiver. Now with Phyllis and Nancy staying with us, I was hoping for a smooth transition to my breast feeding. Even though we scheduled our birth, mother nature had a different plan and Kathy’s water broke as we were ready to leave for the hospital. That threw everyone into a tizzy, but we managed to get Kathy to the hospital in plenty of time. This time, even delivering twins, Kathy had no problems with delivery (I think because of her calm state of mind. Although in the middle of birthing, there wasn’t much calm!) Tracy and Taylor were healthy six and one-half pound baby girls.

Now was my turn. At last, we had come to the finish line. Only one thing remained. I was given the girls one at a time, while I sat in a rocking chair. Tracy was a pro and latched on to my right nipple and began sucking like there was no tomorrow. Taylor was a little hesitant and we needed to wipe a little of my milk on her lips for her to get the message. But soon, both of my breasts had been emptied. It was quite a feeling when my milk first let down. I was almost euphoric. We had planned this for over six months and now it was real.

Beth, Paula, and Gabrielle, and Laura8 were there when the girls were born. Along with Kathy and I and the moms, it was a great celebration. I didn’t feel much maleness as this gaggle of females were treating me like one of them. I was glad that Paula had shown me how to put my hair up. My mom actually was nice enough to put a French braid in my hair to keep it out of my way. I stayed with Kathy overnight so I could nurse the girls, and everyone made plans to take Kathy and the girls’ home from the hospital tomorrow morning. I was now on a three-hour cycle with the twins.

During the night, Kathy’s nurse brought in the twins in their rolling cribs. Nurse Teresa was a big help as I was wiped out. I made it through the night and successfully nursed twice. Nurse Teresa was nice enough to change the babies first, then wrap them up and give them to me. We packed everything up the next morning and Doctor Cyn gave us the all-clear to head home. Dr. Cyn watched me nurse the twins before we left and stood their slack jawed as our breastfeeding plan was finally coming to fruition. ‘Dana, we couldn’t have expected a better outcome. I want to see you in two days at my office, little mommy. I still can’t believe you are nursing. My colleagues couldn’t believe when I submitted my first report. While protecting your confidentiality, my papers have been the talk of the OBGYN community. They are still skeptical that you pulled this off. You may be a trend setter!”

Fortunately for Kathy, having a regular vaginal delivery instead of a C-section made her recovery much, much easier, even though she delivered twins. She had quickly shed the weight of the twins and now was a ball of energy. I was worried about post partem depression, but Kathy was more worried about that for me. We started in with water aerobics and both Emily and the twins loved the water with Kathy and me. We even coaxed the moms into the water with the coffee group and had a great time. I was so happy for Kathy. Her first pregnancy was rife with issues, but she was as calm as a cucumber now. I didn’t realize what was coming next.

I thought I was driving this milk train, but I was soon to find out I was simply a cosmic passenger.

End of Part 9

Dana’s Story, Part 10, just the beginning of the new Dana 2.0

More Changes for Dana and now Kathy’s In-Charge

Dr. Cyn was delighted to see us a few days later. With the moms watching the girls at home, Kathy wanted to get dressed up and go shopping after our appointment. Kathy was in such a good mood, she uplifted both of us. Dr. Cyn was beaming again when we met. She started with Kathy first, “Kathy, you came through that pregnancy amazing. I think your mental health had a lot do with the outcome.” She went on to say that she examined her uterus and ovaries right after the birth and she looked very healthy in both aspects. Dr. Cyn then smiled at me as I sat in the exam chair in my gown. “Dana, I see you’ve dropped much of your pregnancy weight as well. It’s very important for you to stay hydrated while nursing, so at least 8 glasses of water a day. Your breasts are bigger now that your milk is flowing. You need to make sure to air out your nipples after feeding and use this Vitamin D ointment liberally. I would also suggest going up one cup size in your maternity bras.” Just what every man likes to hear!

After thanking Dr. Cyn and making another appointment in a month, Kathy was on a mission. “Dana, we have about two hours of power shopping before we need to get back for your next feeding.” Kathy took us to L&T and fifteen minutes later, I was trying on 38-D nursing bras. She told me to leave the Lilac Lace bra on while she paid for the rest, including matching panties. With Spring just around the corner, we also shopped for summer skirts and shorts. “Dana, I want you to be able to be comfortable showing off your figure once we get our bodies back in shape.” She wanted to find comfortable MILF wear, that we could both enjoy. My now voluptuous breasts were on full display in the new tops we bought.

We made it back home as my breasts were getting uncomfortably full. As I got my water bottle and burping towel, Kathy got Taylor’s diaper changed then handed her to me in my rocking chair. My breasts were so full that Taylor was getting a good flow going quickly. Kathy sat on the sofa with the moms chatting away while watching me. Nancy was holding Emily, who was totally enthralled watching her new sisters. Phyllis was holding Tracy and cooing to her as she was fussy about having to wait for her sister to finish. As I was about halfway through with Taylor, I gently inserted my finger under Taylor’s mouth to break her suction on me. She opened her big eyes at me, and we had a group awww. Kathy took her from me and put Taylor on her shoulder to try to expel any gas. As I put Taylor back to my breast, Kathy suggested trying Tracy on the other side so they could both feed at the same time. I knew this was a possibility from our Le Leche classes, but it was uncharted territory for me. I cradled Tracy in my other arm and Kathy brought her mouth to my nipple. What a rush! I don’t think I could do this by myself but having both babies suckling at my breasts sent me straight to Nirvana.

It was a Kodak moment as I shut my eyes to enjoy the situation. My mom spoke up, “Dana, never in a million years would I ever dream of watching my son nursing my granddaughters. But I feel like you are the most feminine daughter of my children now. You are breastfeeding like a pro and your wife is ecstatic.” The moms stayed a few more days and were a big help.

On their last night here, the adults were sitting in the living room after the girls were all put in bed. My mom and Phyllis were having a discussion about our living arrangements. Kathy joined in as they were all enjoying a glass of wine with me enjoying my water bottle. Kathy was by no means taking over the ‘man’s role’ but she was asserting her Alpha Female side. I was just sitting there contentedly giving my breasts a little breather. Nancy asked, “Kathy are you going back to work soon?” “No”, she replied, “Dana has invited me to stay at home and work with her consulting business.” I had? This was news to me. We had briefly talked about her staying home, but I assumed she would go back to L&T. “We have a new schedule next week to get us back in shape and Dana and Laura and I are going to be reinventing ‘Butterfly Consulting.’” We are? My mind was having a hard time concentrating, but Kathy was laser focused.

Phyllis was next, “Kathy how should we refer to your relationship now?” Was I her husband? Her sister? Her sister-in-law? Kathy looked at me lovingly and said, “Dana is my wife, of course.” I certainly was, and I loved hearing those words come out of her mouth. Kathy’s solution was simple.

That night I found out about the scheming that Kathy and Sandy from Transformation had in mind. Kathy had gone back to Transformations with her own request. They had all of my measurements from before, but the measurements Kathy was giving her put a whole new twist on the story.

I was getting ready for bed after feeding the twins. I took off my makeup and then looked around for my nightgown when Kathy announced, “you are in for a treat tonight, my little Dana mommy.” Kathy had me turn around and put a formidable looking leather corset with D rings on me and proceeded to lace up the back. She then rolled up black seamed stockings on my feet, then put my ballet boots on. She also put padded cuffs on my wrists then snapped them to my waist on the D rings. Kathy then pulled out a box and took out a penis looking vibrator to show to me. “Do you know what this is Dana?” Well I wasn’t born yesterday, I do know what a dildo looks like, but…”No Kathy, what is that?”

Kathy began to give me an anatomy lesson as my brain desperately wanted sleep. “Look at the outside of the penis, Dana. It is an exact replica of yours when we started this journey! Now the inside is what you will really like. Sandy at Transformations used your initial measurements to create the outside lifelike duplicate. She then took an actual casting of my vagina and has put that on the inside of the penis for you!” I was now looking at a life size replica of my penis from months ago and Kathy was getting very excited. She then pulled out another box which had another life size replica on both ends hooked up to a panty. There was also a smaller looking penis with straps attached.

“Dana, let me attach this for you, you are going to love this.” Kathy took a smallish looking cock-ring and pushed it back to the base of my penis (which was limping along). I obviously had no balls to constrain the ring, but Kathy then had me stand and bend over the chair in our room. I could feel her slippery fingers and she was pushing them in my rosebud. The next thing I felt gave me a slight burning sensation. “Dana, just calm down and relax. You will be amazed!” I relaxed a little and felt an obvious butt plug slide in my rosebud. It wasn’t too uncomfortable, but I wondered where this was going. At this point in time, my mind wanted to shut down and get some sleep, but by now my whole body was aroused, my nipples started leaking, too.

Kathy was on me like a tigress, sucking my nipples and raking her nails over me. Then she reached behind me and started the vibrator on the g-spot plug. Wow, my whole body just got a big wahoo. We had never played with bondage before and I love it but was going crazy. Kathy then took the dual ends of the g-spot vibrator and put them into slots in my cock-ring. That woke up little Danaboy. Kathy then lubricated the fake penis and put my own penis inside it. The feeling was incredible! She then attached the end into the remaining slots on the cock-ring. I now had a g-spot vibrator in my backside and my own penis inside a replica of Kathy’s vagina. A perfect fit. The last thing she had for me was the penis gag in the box. With my hands locked to my waist, I was at her mercy. She smiled and said she didn't want us to wake the girls. This was another first for me and I couldn't wait to show Kathy some of the same.

Kathy lowered herself onto the replica of my penis and started vigorously humping me. Now my backside was vibrating my g-spot as Kathy was getting busy. When she leaned over and started sucking on my nipple, I orgasmed like never before. Kathy was in the throes of her own orgasm as she continued to nurse on my breast. This was another check box for me. I totally felt I was in the middle of an orgy. Actually, I was the orgy.

We were in a crazy sexy marathon for the next two hours. There was nothing left as both of our bodies were spasming. Kathy wasn’t they only one sucking on nipples as I was determined to make up for my constant nipple play, by giving Kathy the same when she let me.

The midnight feeding of the twins that night was another erogenous encounter of the third kind. My nipples were on high alert from all of the playfulness from earlier. When Kathy attached the twins to my nipples, I was nearly screaming. Kathy gave me my water bottle and waited to take them off to burp them, then put the suckling twins back on me. Whoa. I don’t even know what box to check on my bucket list for this. Kathy was my biggest supporter and now my Alpha sex wife on our journey.

By the end of the first month of breastfeeding, Kathy and I were getting close to our pre-pregnancy figures. The last step was getting my ‘belly’ removed. What a wonderful experience to have experienced the whole pregnancy thing, but I felt that once was just perfect. Kathy and I were once again ‘twins’ in our shape, (although I had an edge in boobage.) hahaha

Butterfly Consulting Make-Over

The next few days were similar. Kathy would help situate the twins on my nipples and we fell into a bit of a routine. Every three to four hours, they wanted to eat. Kathy was almost fanatical about my nipple maintenance because of her previous experience. All I knew is that breastfeeding my little girls was the most sensual feeling I have ever had. Our sex life was interesting to say the least. Obviously. At this point in time, I was more than able to manage our household while watching our girls.

Laura and Kathy were busy reviewing our clients and network. We were on an upward growth curve and wanted to spread our network to as many women as we could. After our 10am feeding on Monday, we had our first ‘Board Meeting’. Laura started out with a review of the last year. “Dana, if we look at the network we have developed, we now have over 20 solid clients. You are the person that is blazing the trail. But Kathy and I want to be able to develop an operational template that allows us to involve more women.” I thought these two were incredible together, with Kathy’s image consulting and creativity and Laura’s knowledge of our business, they had a great plan. “You two are awesome! What’s our first step?” I saw two devious smiles looking back at me.

“Dana, you have changed the landscape for women in consulting. We need to develop a marketing image for our company,” stated Laura. “You have been a groundbreaker, and we want to highlight that. We want you to be the ‘Face’ of Butterfly Consulting.” My face? I’m a guy. “Dana, we need to project a confidant, take-charge woman. That’s you” added Kathy. “I’m flattered, but what kind of image were you suggesting?” Laura and Kathy had some sketches showing me in different business poses wearing a boardroom suit. When I looked at them closely, they showed me with more of a ‘business bob’ type of hairdo. “Kathy, I don’t want to cut my hair. It’s taken me so long to get it to this length.” Kathy and Laura looked at each other with a sly smile, then looked back at me. “Okay Dana, if that’s what you want to do, we have a backup proposal.” Was I really that stupid? My brains must have been leaking out with my milk.

The ‘backup proposal’ was really the main goal of the co-conspirators. “Okay, I will do whatever you two want, but where are we going with this?” Their idea was for me to be the ultra-feminine look, with the two of them portraying working women. “But doesn’t that defeat our purpose?” “No Dana, we want to project that women can have a business look, but also show they still enjoy being women. You are the epiphany of womanhood.” She showed me the nails that I would be sporting as our image was developing. They were long and pink and had a butterfly design over the middle two fingers. I loved it!

Whoa, whoa, whoa. When did my grand design go off the rails? I am now the ‘face’ of our company? I just took a dive off the deep end of the estrogen pool and I don’t think I’m making it back to the surface. “Since you want to keep your long hair and nails, we want to highlight that in our approach.” They brought out the ‘real’ marketing plan with our goals and desires to help women. And there I was in my LBD with my hair all curled and halfway down my back. I had a determined look, but one that radiated ‘feminine’ by all accounts. I looked more like a runway model (albeit a well-endowed one.) “Dana, we need to go further in our approach. We want to empower women to dress for success. Whether that means jeans or skirts or dresses, we want to help women move forward in business. We have a marketing consultant coming in tomorrow to help.” These girls are awesome. I was now extremely happy that Kathy had decided to work with us. She had such a creative mind and helped us keep on point on our goals.

But later that day I was sensing something was bothering Kathy. We were usually very open and honest with each other, so I thought she would tell me in her own time. As we were getting into bed, Kathy looked at me with a very serious look on her face. My first thought is the thought of every CD out there, ‘she was fed up with her ‘feminine’ husband. But her look turned to one of confidence as she started to explain. “Dana, we have gone through a lot in our short marriage. I think we both know we have found our soulmate. But now our marriage has taken on a different twist. You are now presenting as a woman and breastfeeding mother 24/7. I hope that you take what I’m about to say seriously.” Are you kidding? After all we have been through?

“Dana, I want you to be my wife and our children’s mother! If other people don’t like it, too bad. I love this new you. I love your sacrifices for me. I really love your new boobs, especially when I am thirsty. And I love your new body and long hair and long nails. What do you say, Dana?” “I say, YES, YES, YES.” I couldn’t have asked for more. My wife was now fully invested in the new Dana. That was a great load lifted off my mind, it was always nagging me.

The first thing the next morning, we were all packed up and headed back to the Gurlz Salon and Paula. We were hurrying to try to get everyone there on time, but the first thing that needed to happen when we arrived was to feed the twins. Everyone at the salon was excited to watch me nurse. I was getting used to the routine now but having two hungry girls sucking like vacuums still gave me mommie-gasms almost every time. After the twins were done, they were taken from me and I dutifully followed Paula back to her station. “Okay Dana, just sit back and relax. We are now going to Dana 2.0. First stop, hair.” Kathy and Laura had this vision of some Hollywood starlet for me. Okay, I hate this (hahaha) but I’ll do whatever is necessary to become Dana 2.0.

“Dana, we know you love your long hair and long nails, even though that is somewhat impractical for a young mother. But we want to play off of that image and give you a ‘models’ look. We want to take the mother image to a whole new level.

We are going to start by putting quite a few extensions into your hair. I know your own hair is long, but in order to achieve Dana 2.0, we need a lot more hair. Secondly, we are going lighter with your highlights to give it a more youthful, flirty look. My longish looking hair was now tickling my derriere. My hair was going to be taking up quite a bit of my time. I was in a whirlwind of femininity and I was enjoying every second of it. I couldn’t wait to see what was next for us.

End of Book 1