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