The Rose in Winter
Copyright © 2012 Jenny Sugar
All Rights Reserved.

Terry Simpson trudged along the snow-covered sidewalk to his apartment. In his arm was cradled a paper bag with a fifth of Johnny Walker. He looked up at the darkening skies and knew that the forecast of snow for Christmas was an accurate one, for once.

His 24th Christmas, to be spent alone, as most of them had since graduation and finding employment. He entered his drab apartment and fished the bottle of liquor out of the paper bag and set it on the kitchen table. Tossing the bag, he paused, thinking that perhaps tonight he’d let his true self out for a while.
Deciding that since there was no work tomorrow for him, he might as well do it, he headed for the second bedroom. He kept it locked, for obvious reasons, and unlocked it and turned on the light.

Rather than a bedroom, this room looked like a woman’s walk-in closet. Two department store type metal racks on wheels were both full of dresses and two and three-piece outfits. A large shoe rack graced one corner, stuffed full of flats, heels, ankle boots, and tons of pumps. A large dresser was in another corner, with a large oval mirror and to one side, a lighted makeup mirror. Makeup was lined up in a rough sort of order all over the top.

Articles and how-to guides of every sort of makeup and hair tips were taped to the edges of the mirror on both sides, most cut from teen girl magazines. Three shelves were to the right of the mirror, all held foam heads sporting various types and colors of wigs. On the back of the door was attached a mirror, as well, the kind a woman could check her entire look in.

He looked at himself in the door’s mirror, seeing a very skinny (for a man) person with no body fat to speak of. A brown mop of hair (unruly and rarely combed or brushed) topped a head with an oval-shaped face. A very feminine face, even without makeup or the earring studs he currently had in. They would be replaced with large hoops later on this evening as he left Terry the man behind and became Terry the woman.

Terry was five and a half feet tall, which helped him pass as a woman on the very rare occasions he went out en-femme. He’d been dressing in women’s clothing since he was twelve and was allowed to be home alone for the first time. His mother’s smaller dresses, blouses, and one of her fur coats were all fair game as he indulged his perversions (as he thought of it at the time.)

Inevitably he had been caught by his mother and screeching and accusations of Terry being gay had followed. His mother had always worried when he was younger because all of his close friends were girls. She blamed herself for divorcing and raising him without a father.

Over time things had calmed and he’d never touched his mother’s things again. Instead he’d gotten a locking trunk in the bottom of his closet and started buying his own things. College was not much different, and he only stayed long enough to get an associate degree. This led to a decent job at his current employer, developing software for automated controls. Unfortunately the job was not a high-paying one, and between high rent, paying his student loan back, and food his only real frills were his secret items he stored in the spare bedroom.

As Terry slipped on each item of clothing, he started feeling happier and “he” became “she”. She sat at her makeup mirror and expertly applied foundation, translucent powder, mascara, eye shadow, lipstick, and worked her hair into a decent style.

When she was done, she stood in front of the mirror and was pleased with what she saw. Every time Terry dressed up and went out on weekends was a grand adventure. She was quite proud of the fact that due to her feminine features she was never “clocked” by anyone as a “tranny” and passed as a woman completely.

She wandered into the kitchen and was about to open the fifth of whiskey when she heard a knock on her door. Slightly alarmed by the knock, she slipped over to the peephole and looked out. Swirls of snow blew around a woman standing at her door, in what looked like a fur coat. She slipped the chain on the door and opened it a few inches.

Without the distorting view of the peephole she could tell that the woman was a cross-dresser, as the planes and shape of her face showed. She was wearing an expensive fur coat.

“May I come in, Terry?” the obviously cross-dressed woman said. “The snow is really coming down out here; I’d like to get out of it!”

Terry was horrified that this person knew her name, and thus her birth gender, no doubt. But, compassion and her inner sweetness forced her to step aside and gesture the stranger into her home.

The woman was in a floor-length expensive mink coat. She shrugged out of it and hung it on Terry’s coat rack carefully. She turned and Terry got her first good look at the woman. Her face was angular and obviously male, her biggest giveaway. She looked to be around sixty years old, perhaps older.

Her wig was one of the more expensive ones, certainly. Her dress was a designer dress, Dolce and Gabbana, if Terry was any judge. Much more expensive than anything Terry could afford. For Terry, a nice dress involved shopping online at discount shops.

“You may call me Roxanne, Terry. Thank you for letting me in tonight. I drove here to speak with you about something important. I had no idea I’d be caught in such a blizzard or I’d have waited for another time!”

Roxanne was softening her voice but it was a baritone that no amount of softening could fool anyone at all.

She spotted the bottle of liquor on the table and turned back to Terry. “A bottle of whiskey and an empty apartment on Christmas Eve, Terry do you know how sad this looks?”

Terry nodded, and offered to share it with her unexpected visitor. Roxanne smiled at Terry and accepted her hospitality, and remarked, “I know much about you, Terry. And I know that at heart you are a good person. You invited me in your home without even knowing who I am.”

Terry got two glasses out and poured them each about half a glass. She ushered Roxanne over to her living area, which consisted of two comfortable chairs, a small coffee table, and little else. They sat down and Terry waited to hear what Roxanne had to say.

She sipped her whiskey with a grimace, and sat the glass down on the table. “I am getting short on time, these days, and I wanted to visit with you while I could.”

Terry looked at her uncertainly and responded. “How do you know me, Roxanne? Who, exactly, are you?”

“Who I am is not that important, Terry. Why I am here is. I’ve had you checked out and I have also watched you for some time. You are living a lie, Terry. A miserable existence at best, and worst of all, you know this, don’t you?”

Terry was startled and a bit unnerved by what Roxanne had said. “Umm, Roxanne, that worries me a little you know. I try to keep to myself and it seems you know all about me?”

Roxanne waved her hand and dismissed his concerns. “If the mink coat didn’t convince you then the Mercedes outside probably wouldn’t either, Terry. I am quite wealthy and not some random stalker or tranny psycho looking to stab you for some money to get a meth or crack fix. I am here on your behalf, really, not my own.” She bent over coughing and took a sip of her drink before continuing.

“In my life, Terry, I was so much like you. I knew I was different, I learned over time of the woman inside me. But, look at my face, my height, and my broad shoulders. I could never be passable and worse yet, I knew it. Nothing that I could do and it made me a very bitter man. I used that bitterness, though. I focused everything that I had into my work and never allowed myself a personal life. Outside of the random call girl here and there, I never had a sex life, either.”

“My marriage was a joke. Sure, I loved my wife, but things just didn’t work out well at all. She got a huge settlement and left rather happy with it all. And I? I threw myself back into work, of course. That’s the first thing that I wanted to share with you tonight. Don’t ever let work take over your life, Terry. You need balance! I never ever had it.”

“Am I to be visited by three ghosts, later?” Terry asked facetiously.

Roxanne tilted her head back and laughed. “Good one! No, just me, Terry. Just me.”

“Look at you, Terry. You are far more passable than I ever was, and you don’t even have to work at it that hard. You look just like an average woman right now. But you refuse to go further with it. You work, you come home, and you dress up a few nights a week. Lather, rinse, and repeat week after week — till you retire and die. That’s not a life, Terry.”

Terry shrugged uncomfortably. “I have to work hard, or starve. I don’t have any friends really and even if I did I’d have to hide my cross-dressing from them. And if word got out at work about my little habit, I’d be ridiculed, or ignored or even fired.”

“Focusing on nothing much but work and indulging my dressing habit has left me fabulously wealthy but sad and unfulfilled. I see you on the same path, Terry.”

“I don’t seem to have a problem with being fabulously wealthy, you know. Look around here and I think you can see that,” Terry replied, slightly bitter.

Terry’s reply only made Roxanne roll her eyes. “Sure, you’re starting out, and I’ll admit that times are hard right now to make a start. You miss my point, though, kid. Wealth is nice but in the end it is worthless without someone to share it with. Or, at the least, having fun yourself with it!”

Terry nodded. Roxanne went on. “Here you sit on Christmas Eve, alone, with a bottle of liquor and little else. Your life is an endless loop, Terry. Sleep, eat, go to work, come home, sleep, and eat. You have no friends! Why do you not have friends, Terry?”

Terry looked both angry and uncomfortable with the question, but finally snapped out, “Because I can’t find any friends worth having!”

Roxanne sadly shook her head. “You can’t find any friends that you want to share the real inner you with, you mean. You’re a woman inside, but live as a man in a man’s body. It is your deepest and darkest secret, and one that you feel would drive away anyone who became close to you. Am I right, Terry?”

Terry eyes begin to water and tears escaped, which she quickly brushed aside. “Look, Roxanne, all of that may be true but what is it to you?”

Roxanne pointed at herself and ran her hand along her own body. “Look at me, Terry! I know how it feels! But, I have never been completely passable like you. You have the opportunity to go for it! You can become your inner woman, not sit trapped like I have for years and cross-dress in secret!”

Terry glared at her visitor. “You think it’s that easy? Hormones cost a fortune. Breast implants are not free. And, genital reassignment surgery? Hah, forget about it. I’ll never be able to afford such things.”

She paused and took a belt of the liquor, then went on. “Besides, if I tried to transition, I’d lose my damn job and then I’d lose my apartment and end up on the streets. Don’t you see, I am stuck right now, I can’t do a thing about this even if I wanted to.”

“You’re only stuck because you won’t take the first step,” Roxanne replied.

“Yeah, and how would you know anyway? You said you are wealthy. What do you know about making ends meet, about being one paycheck away from homelessness?”

Roxanne replied softly. “I was poor, once, with no food, no home, and sleeping on a cousin’s couch. But I never stopped trying, and in the end I built my own company and had amazing success, Terry.”

“Well goody for you, Roxanne. Maybe one day I will get a shot at the brass ring and then we will see, won’t we? But until then, I guess I will just live with things as they are.”

Roxanne went from another angle. “Why are you not in a Transgender support group, Terry? There are many of them in this area, and you could go to meetings in one of the neighboring towns if you’re afraid of being seen.”

Terry sighed and took another sip of whiskey. She glanced out the window at the swirling snow a moment before answering. “I’ve tried those, and it was okay I guess but it didn’t help me get anywhere. The people were nice but they couldn’t make my life better. I prefer to make my own way rather than dump my problems on a bunch of strangers, besides.”

“I know you are very independent, Terry. I know much about you and I think you will do well in life, if you are given a small push to get you on your way.” She seemed to come to a decision, and set the glass down and looked earnestly into Terry’s eyes.

“Terry, the doctors tell me I have one to three months, at best. I’ll be bedridden and unable to do much soon, as well. I wanted to meet you once, and tell you that I am leaving you some things to help get your life to where it should be.”

“Things? Roxanne, I don’t understand?”

“It’s all in my will. I don’t have kids, and I don’t even have cousins or nieces or nephews to leave anything to, so when I noticed you and found out your situation, I thought you’d appreciate a little help.” For some reason Roxanne grinned when she said this.

“But… I don’t even know you! This is… crazy!” She laughed, thinking this was like some kind of bizarre alcohol-induced dream. Rather than Santa on Christmas Eve, she got a strange old tranny in a fur coat promising riches when she kicked off.

Terry’s face must have revealed her thoughts because Roxanne chortled. “It sounds crazy, but there you go, it is true. Anyway, Terry, I want a promise from you, one that you will keep. If I leave you the wherewithal to do all of those things we spoke of, including the GRS, I want your solemn oath that you will do it. You are like a rosebud right now Terry, and I am simply providing the help to make you bloom into a beautiful rose. Will you do that, Terry? Will you bloom for me?”

Terry didn’t have to really consider her response. “Roxanne, if you are telling the truth and you were to leave me enough to do all of that, then hell yes I promise I will do it! I’ll do it all, the hormones, the breasts, the GRS… yes, I swear that I will do it! A new start, as you said.”

Roxanne smiled and took Terry’s hand and held it in both of hers. “That is all I ask, young lady. Don’t sit in silence and loneliness, get out there and be the vibrant happy woman that I never could be. Oh, in the will you are going to be listed as my niece, so keep that in mind, okay?”

Terry nodded, understanding Roxanne was going to make sure her niece was the one inheriting the money. A final push from beyond the grave, as it were.

Roxanne stood and Terry helped her into her fur coat. She looked out the window again, and while it wasn’t a blizzard any more, there were still flurries coming down. Christmas morning would be beautiful. “Are you sure you don’t want to stay? The streets might be rough…”

“Thank you, Terry, but I must be going, honey.” She pulled Terry into a hug, and Terry could feel how bony and wasted her body was when she returned it.

Roxanne paused before going out the door. “I feel really good about you, Terry. You’ll be contacted by my lawyer when I pass. Please, use what I leave you to live a full life as a woman, and never forget to enjoy life. It is gone, before you know it. Goodbye my friend.”

Roxanne walked out the door and as Terry watched, went up to an idling Mercedes, where a driver popped out and helped her into the passenger side. The car left, and Terry closed the door and sat down, still amazed at what had happened.

Terry spent the rest of the evening watching the snow fall and taking an occasional sip from the bottle, occasionally thinking about the odd visitor.

January ran into February and the Valentines were all over the office doors and cubicles for the approaching holiday. Terry had an office now, a small one, but it had a door and offered some privacy.

She’d almost completely forgotten the strange Christmas Eve visit from Roxanne, and even if her visitor had been sincere, Terry did not like the thought of coming into a little money due to her passing.

Terry was about to dig into a batch of reports when someone knocked on her office door. She yelled out “Come in!” and a man in a very expensive suit walked in and closed the door behind him. He walked over to her desk and offered his hand, which Terry took.

“Miss Simpson, my name is Leonard Paulson, and I am an attorney. My firm is probating a will, and you are both the beneficiary and the executor of the estate.”

So it was all true! Roxanne was not pulling my leg! She actually left me a little money, it seems! Terry’s face must have revealed his shock, because the lawyer smiled a knowing smile.

“Yes, he said that you’d be surprised when I came to see you. Miss Simpson, you’ve been left the entire estate of James Montgomery, and that includes his home, his company, and all of his possessions. He left some small amounts to certain individuals, but the bulk of it is now yours.”

Terry felt faint and gasped. “That James Montgomery, the CEO and owner of this company?!”

Paulson nodded, and replied. “Yes Miss Simpson, that James Montgomery. You own this company now!” He grinned at her. “Congratulations, Madame CEO!”

If Terry had been standing, she’d have had to sit down in a hurry. Her head was spinning and her breath was caught. James Montgomery was worth millions, and supposedly had a very luxurious estate.

Paulson looked hesitant for a moment, and then plunged onward. “There is a codicil, a secret one, that we need to discuss.”

Terry nodded, already figuring out what was coming.

“The Will specifically leaves everything to James Montgomery’s niece, Terry Simpson. The codicil states that you will legally change your gender to female and live as his niece. He told me that this was discussed and you had agreed to it previously. Is this still true?”

Terry didn’t have to think about her answer. “Yes, completely and totally, I agree to the terms.”

Paulson smiled happily. “Good news! I am pleased that this will go smoothly, then. I am to help you with everything, which is also in the codicil. Plus, James asked me personally to help you in any way that I can, and I will honor his wishes.”

He began to rummage in his briefcase and pulled out a folder, which he then handed to Terry. “In there you will find everything pre-arranged for you. James found you the very best doctor in the field, and has set everything up in advance. All you need do is show up, basically.”

Terry flipped through the documents, and found a birth certificate with “Terry Montgomery” on it, listed as a female, with his own birthdate. He had to sign some papers, including medical releases and forms for a feminization specialist. He asked the lawyer about it.

“Oh yes, Terry. James searched high and low and found the absolute best doctor in the field of GRS and feminization. All of the fees are prepaid, so you are good to go.” He stood and offered his hand, and Terry shook it. “I’ll be in touch, Terry. As for your position at the company, I’d suggest that Terry Simpson turn in his resignation today.”

Terry nodded in agreement, and went and sat down at his computer. There was an all-employee email detailing the death of their CEO and also mentioning his replacement: a niece of Montgomery’s named Terry Montgomery. Apparently she was the daughter of Montgomery’s deceased younger sister.

Terry’s head was spinning from all that was happening. He decided to quit his job, first, then go ahead with the plans he’d been given. Quitting was not a big deal at all, as his boss was facing losing a few people in his department by attrition anyway. He promised Terry a good reference and wished him well. Terry left with a small cardboard box of items and a wave.

The next three months were a complete blur to Terry, who had multiple surgeries, voice coaching, feminine coaching, and tons of paperwork to sort through. But, over time, the woman within emerged like a butterfly from its cocoon.

Eventually Terry Montgomery took the helm of her deceased uncle’s company. She also settled comfortably into his beautiful home, and enjoyed settling in to her new identity.

Terry did well, and was able to rely on Paulson for advice and help with any and all legal situations and quite a few business decisions. She decided to follow Montgomery’s policies and plans as much as possible, without rocking the boat too much. Terry was finally happy and her exterior matched the woman within. A confident and happy woman, everyone could see that.

Terry sat in a private room in her beautiful home; staring at a portrait of James Montgomery dressed and made up as Roxanne. It was Christmas Eve again, and once more it was snowing outside — thought not nearly as hard as it had been that fateful Christmas Eve one year ago.

Terry sipped a very expensive wine and raised her glass to Roxanne. “You saved me from a sad and lonely life, Roxanne. Without your generosity I’d still be sitting in that apartment wishing for what I could never have.”

She stood, revealing an expensive dress and jewelry. She was heading to a Christmas Party, and looked forward to it. The old Terry would never go to a party, nor would get close enough to people to even get invited to one, really. The new Terry was making friends, cautiously, but making friends.

“Thank you Roxanne, for everything. I’ll never forget you, and I will try to live my life to the fullest and honor what you did for me. Merry Christmas, Roxanne!”

Terry turned out the light, and headed out to enjoy herself, and bloom.

Just remember, in the winter
Far beneath, the bitter snow
Lies the seed, that with the sun’s love
In the spring, becomes the rose