Copyright © 2021 by Madison McCall

  All rights reserved

  No part of this book may be reproduced in any form or by any electronic or mechanical means, including information storage and retrieval systems, without written permission from the author, except for the use of brief quotations in a book review.

  This is a work of fiction. Names, characters, business, places, events, locales, and incidents are either the products of the author’s imagination or used in a fictitious manner. Any resemblance to actual persons, living or dead, or actual events is purely coincidental.

  Madison McCall

  Chapter 1

  “Come on Jeremy, why not? Besides, a few days away would do you good, and after all, you’ve earned it,” then bending down and whispering he said, “A lot more than some of your co-workers that are just here collecting paychecks,” then raising back up and scanning the room he continued, “I can’t be saying stuff like that or surely someone will be offended because I didn’t say they were good workers too.”

  We both laughed briefly and I leaned toward him and said in a low tone, “I promise not to tell a soul Clay.”

  Clay was my boss and was a man with graying hair, in his mid-fifties, twice divorced and currently single, and it was not uncommon for him to go off on a tear and rant about whatever was on his mind at any given moment in time. He had been my manager during the three years I had been with the firm and was a good guy to work for and had always treated me fairly. However, everyone did not feel that way and I suspected the reason was because he was old school. When I use that term it is in the sense how many of my contemporaries, millennials, saw him. He was traditional because he expected you to show up, on time or thereabout and actually work. That was fine by me because I loved my job as a technical writer and really enjoyed my work. Plus, staying busy always seemed to make the time pass faster, and I’ve had many a day where I looked up at the clock and it was time to go home, which beats of day of drudgery waiting on the whistle to blow so you can leave.

  Nodding once he said, “I appreciate that, because the last thing I need is to have someone running to HR complaining that they are in a toxic environment. I swear to God, sometimes I think we ought to get rid of all the management and let those son-of-a-bitches in HR run the place.”

  Cutting in I whispered, “That’s bitches I believe.”

  We both chuckled briefly as we knew there wasn’t a single solitary men that worked in our human resources department, making his statement son-of-a-bitches incorrect.

  Scanning the room he said, “Yep, and you know what? Women are taking over the world, slowly but surely. Jeremy, in a few years we will be completely redundant as men, useless, and will be relegated to certain classes of jobs, and will be the ones staying home raising the kids. Well hell, that may be okay, because when it comes to housekeeping I can do a better job any day of the week than either of my ex-wives did so just slap a skirt on me and call me Sissy.”

  We both chuckled and I then shook my head and asked, “So boss, as you were saying?”

  Rolling his eyes upward briefly he then looked back at me and smiled and said, “Branch Global is one of our best clients and they absolutely love the work you do and say you’re the best tech writer that’s ever done work for them. So, with that being said, plus the fact that they are getting ready to pick up a couple of new clients, according to the rumor mill anyway, and will be in need of the work that our company just happens to perform….” He said as he smiled and threw his arms out to the side with his palms open.

  “This doesn’t sound like what I do, but more like a sales call.”

  “Look, the sales guys don’t always know all the technical stuff, and you do. I think after they meet you, we will be a shoe-in to pick up their upcoming contracts. Look, you’ve got the sales guys beat to hell as not only do you know the tech stuff, but you’ve got a great personality, you’re neat, clean, well dressed, and articulate.”

  Shaking my head, I said, “I’m not really the schmoozing type boss, I’m more the quiet tech guy in the back room.”

  Hunkering down beside me he said in a low tone, “Your review is coming up soon, and along with it comes the potential for a raise, especially if they approve our RFP’s and we pick up their contracts. Plus, you’re not out of pocket on any of this, the company will pick up the entire travel tab so what do you have to lose? So, as the Italians would say, capiche?”

  I think the actual Italian word he was trying to use was capisci versus the Americanized version he was attempting to utilize, however, I understood what he was trying to say and felt it would be rude to correct him, especially since he was my manager and there was no need me being a smartass.

  Shaking my head, I then rolled my eyes upward before looking at the floor and then returning my gaze to him and asked, “And this would only be for a few days? If that?”

  A smile came to his face and he said, “Super, Jeremy, you’re the best. Yes, two, maybe three days, it’s up to you. You’re going to do great, just visit with the staff and management, get to know them, answer any questions they might have, and oh, if they mention anything about upcoming projects don’t hesitate to say, hmmm, that sounds interesting, and maybe they will.”

  Waving my hand, I said, “Okay, I’ve got it.”

  “Cool. Oh, why don’t you think about going out mid-week and then taking a long weekend and explore the area. I understand there are two quaint little towns not too awfully far from the city where you will be, both about forty-five minutes away, North Point and Center Point, oh a place called Four Points too. I swear to God, where did they come up with those names? Anyway, from what I’m told they are all pretty cool and have antique shops, B&B’s, sidewalk cafés, and all kinds of touristy stuff, you could even take your girlfriend if you want, what’s her name? Heather?”

  “That’s right, it’s Heather.”

  “Oh, by the way, I’m also told that they are so impressed with your work that Haywood Branch himself wants to meet you.”

  Leaning back in my chair my eyes widened and I asked, “You’re kidding?”

  Shaking his head, he said, “Nope, that’s what my friend at Branch Global told me anyway.”

  “Clay, I don’t know what to say.”

  “Just say next week is fine Clay.”

  Rolling my eyes up toward the ceiling I shook my head and then repeated his words, “Next week is fine Clay, and I hope I don’t regret letting you talk me into this.”

  “Super, we’ll iron out the travel arrangements this week and thanks again,” he said. Walking away he turned back and looked at me, smiled and said, “You’re not going to regret this Jeremy, and even if nothing else comes out of it you can say that you got to meet billionaire Haywood Branch. That’s got to be worth something.”

  “That’s true.”

  “You never know, this could be a life changing event for you.”

  “I’ll believe that when I see it.”

  Turning back toward my desk, I continued with the project I’d been working on before Clay interrupted me. Our conversation hadn’t cost too much time but had broken my concentration. Well, no matter, I would just have to get back on track and hopefully none of my other co-workers would take a notion to stop and visit with me since I had a deadline to meet. I liked all of my fellow employees, really and truly I did, but sometimes I wondered what on Earth was going on in their heads as we were there to work and were actually being paid for it as well. I was frequently subject to being forced to watch online videos which they thought were funny as they were laughing hysterically through the entire thing and they had already seen it multiple times. Why would anyone think that I would even remotely be interested in seeing a social media page with a meme of a cat saying something which they thought was clever? Sometimes I suspected that they believed the cat actually said the thing on the meme.

  As I sat there looking at the material that I had been editing I could not help but think about the comment that Clay had made about the trip being a life changing event. I’m sure he threw that in just for good measure and to try and make the thing sound interesting so I wouldn’t bail out at the last minute. However, at that moment I had no idea how much truth his innocent statement held as I would soon be faced with a choice that I couldn’t possibly imagine, even in my wildest dreams.

  Chapter 2

  After a full week of hard work, Friday afternoon arrived and despite the fact that it was only 3:30 p.m. Clay told me to go ahead and take off for the weekend. He was a nice guy but not that nice of a guy and I knew the reason behind the offer. I had agreed to make the trip to Branch Global the following week to schmooze, so our firm could potentially get future business. What the heck? You wouldn’t find me complaining about getting off of work a few hours early. I was caught up on everything and there wasn’t anything that couldn’t wait until Monday morning.

  It was pretty common for my girlfriend Heather and I to get together on Friday evenings, however, since her best friend from high school was in town and they hadn’t seen one another in years they were having dinner together versus us. So, that meant I would be spending the evening by myself, aka batching it, and I was okay with that as I did enjoy the pleasure of my own company.

  Arriving back at my apartment about 4:30 p.m., I threw my backpack on the kitchen table and decided that since I had the evening to myself, I might as well settle in and get comfortable and spend some quality time being me. Now, when I say being me, I’m talking about something that very few people know, something I keep to myse lf, information that I guard closely and is very private. It’s not something that I felt ashamed of deep inside nor did I have any sort of guilt about it, however, society is not very accepting of it. My secret was that when I was home alone, I would turn Jeremy the man off and put him away for a bit and permit the real me come out. That’s when I would become Andrea. I was what society might refer to as a crossdresser.

  Personally, I had always thought the term crossdresser was offensive, and I’m not just saying that to add one more thing to the overly long list of things that offend people in the world today. If you think about it a few decades back women were not allowed to wear pants but were required to wear dresses or skirts, but now that they can so is that not crossdressing as well? They can wear their hair long or short and that’s okay but if a man wears his hair long that’s considered inappropriate or feminine. Essentially females can wear anything a man can and that is acceptable, but men can’t wear anything remotely feminine, but I digress. That’s why I say the term is offensive because it is a double standard and defines a man who does so as feminine, a pervert, or unmanly and I personally feel it is an unfair term.

  My desire to partake in clothing normally worn by the fairer sex didn’t happen overnight, no, no, no, it started long ago, and for all of my twenty-eight years on planet Earth I have loved all things feminine and couldn’t help myself. My earliest memory of partaking of female apparel goes back to when I was a child playing with my sister, who was exactly one year older than me. She and I spent long periods of time together and I fell right into the activities that she was interested in which included playing with her dolls as well as participating in playing dress up. Since she was older than I was it always seemed that she had a dress that would no longer fit her but did me and most of the time a pair of shoes as well. Sis also had a blonde wig in her inventory of goodies which she rescued from mom’s giveaway box and subsequently I ended up wearing it as she said I looked better with long hair when wearing a dress. A point which I could not argue. We were the best of friends and were practically sisters as we painted our finger and toenails together and giggled while looking at teen magazines and talked about how cute the boys were. Personally, I was too little to be attracted to males or even females for that matter and I was just going along with her as I wanted to fit in with sis and seem cool.

  As we grew older and stopped playing dress up, I never lost my fascination with femininity and anytime I was alone at home I would sneak into my sister’s room and try on her clothes and marvel at myself in the mirror and think of how pretty I felt. As I would smile at myself in the looking glass I would dream of how wonderful being a pretty young woman must be and wished with all my heart that I could be one as well.

  By the age of 20 I was a sophomore in college and had moved out of the house and got my own apartment, which was something I had wanted for a long time. Now I was then able to fully explore the girl inside of me, who was dying to be unleashed. I wasted no time getting started as the desire had been burning inside me for years and if I wasn’t at school or work I was enjoying the new experience of living as a woman.

  The internet made obtaining my wardrobe easier than ever as I didn’t even have to go to a store. I could buy everything that I needed online and have it shipped directly to me, avoiding the embarrassment of trying on women’s clothing at a retail store. In addition to apparel, I was also able to purchase wigs, undergarments, makeup, nail polish, accessories and shoes as well and in no time I had everything that I needed, and with free returns it was no problem if I got the size wrong.

  For a long time, I had felt that my body hair was offensive as well as unattractive and definitely wasn’t feminine and in my opinion had to go. That feeling actually went all the way back to high school when I began to use an electric trimmer to keep my body hair short as I didn’t like the way that it looked and felt. During summer breaks from school, I would shave my legs as well as my underarms as I absolutely loved the look and feel. I could clearly recall thinking of how lucky girls were being able to have smooth thighs and calves and wear pretty dresses showing off their beautiful, smooth, silky legs and how I envied them and wished I that I could too.

  I soon began shaving off all of my body hair, or almost anyway. Since I was not a contortionist it was impossible for me to get absolutely all of it so I had to have some assistance. With the resources available on the web, I found a lady online who was able to help and I would see her every couple of months for a B and C as I liked to call it, aka, back and crack. With that taken care of I was smooth from the top of my shoulders to my feet and had smooth skin which delighted me to no end.

  Finally, after so many years I was able to dress as a girl and it was just as wonderful as I imagined it would be. It became commonplace that when I arrived home each evening Jeremy turned into Andrea, which was a female name I selected for myself as I had always thought it was beautiful and feminine. Each and every time that I transformed myself I would stand in front of my full length mirror and examine myself from head to toe and I was happy, really and truly as it was as though the real me was finally looking back.

  Despite the fact that I was able to live as a woman in my spare time, privately anyway, I was still not all that confident because I didn’t feel totally passable as a girl and I felt a few of my features were too masculine. For example, I thought my jaw was a little too square; my nose was slightly larger than a lady’s might be, plus, the frame of my body was nowhere close to petite. Perhaps I was my own worst critic but it was what it was. Anyway, I was absolutely dying to dress up and go out in public but at the same time was scared to death and was worried that someone might notice me and then start pointing at me and saying, Hey, that’s a guy! and the prospect of that horrified me.

  I also explored some online groups where men that liked to dress, as I will call it, got together and socialized, and that sounded like so much fun, but at the same time I was self-conscious as I still didn’t feel that I was completely passable. Plus, what if I ran into someone that I knew? What would I do then? Until the day arrived where I had the courage to make my public debut I would have to settle for the company of my likeminded social media friends and there I would be protected under my screen name without anyone from work ever knowing. In this virtual world of T-Girls, as we referred to ourselves, I could take photos of myself dressed as Andrea and share them with my online girlfriends, just as they would do with me. It was truly a place where I could exist as myself, all the while being fully accepted for who and what I was and there were so many other girls just like me, each with their own story and many at different stations in their journey which were too numerous to mention. The one thing that so many of us had in common was that we wished we had been born as a member of the opposite sex, and desired with all of hearts to be able to live openly and freely as such.

  It was clear that I was my own worst enemy as far as making a public appearance as Andrea. I was clearly worried to death of what everyone else thought of me and with that I ended up staying to myself and only lived as her in the privacy of my own home. Still, deep down inside, I was yearning to be able go out in public wearing a pretty dress and heels while carrying a beautiful handbag on my arm. In my fantasy I am out with one of my girlfriends and we are having lunch or maybe coffee and chatting as girls do. I then just happen to catch the attention of a handsome businessman who has dark hair and is wearing a blue suit that can’t help but notice me as he passes by. As I feel the sensation that someone is looking at me I put down my coffee cup and turn and notice that his gaze is moving up the length of my legs. My dress is a little bit short but I knew that when I put it on that morning as I had been secretly hoping something like this would happen. Finally, our eyes meet and when they do we both smile at one another at the same instance, however, this is short lived as he continues walking and soon disappears around the corner of the building. However, that’s okay as I am thrilled at the attention I received, simply because he thought I was pretty. My girlfriend takes notice and remarks about how he was checking me out and we both giggle and talk about what just happened as only girls do.

 

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