Tom and Mary

Author's note: This is going to be a story that has a long build up before I get to the sexual aspects of it, some of which are quite intense. So I ask for your patience as you read it. I hope you enjoy my efforts.

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Let me begin by introducing myself. My mother and father named me Thomas Martin Kendricks, though I haven't gone by the name for a very long time. Be that as it may, I just go by Tom. Well, part of the time that is. I also go by another name. Mary to be exact. No, I'm not a cross dresser or a transvestite or even a transwoman. I'm a shapeshifter. Pick your jaw up off the floor, you read that right. And before you get ahead of my story here, I'm not someone who can just change into anyone at any time. I'm not like Mystique from the X-Men. My ability is very specific. I'm either Tom or Mary. That's it. I can shift at will with just a thought. It's as easy as taking a breath.

So now that you know my secret, let me start from the beginning. Quite literally my birth. I was born February 9, 1913. I am indeed over 100 years old, even though physically I look like I'm in my late 30's currently. I was born in the Northeastern part of the United States. The night I was born there was a meteor shower happening at the same time called the Cyrillid Shower. Now I do not know if this occurrence is what caused me to be different or not, I'm just pointing out the coincidence of it. I studied that shower for decades and finally gave up as I found no proof one way or the other. At this point, it doesn't matter. All I know is I'm unique and I've not found anyone like me anywhere else in the world. And, trust me, I have looked!

Not too soon after I was born, my father moved us to the Midwest. His family was from there and he moved back to take up the family business, a couple of general stores and 4 bars, which outwardly changed to music venues once Prohibition was the law with illegal booze being sold out of the back room. We weren't rich, but we were very well off. Even when the depression hit, we weathered it quite well. People needed their alcohol! But, as I grew up, I was your typical boy, with no hint of what would occur years later.

Fast forward to when I'm 19 years old and I'm college. Up to that point I had no idea what I could do. However, it was that time period that my life changed forever. I'll never forget the note that my professor was handed by a cute redhead. He called my name, asked me to gather my books, and told me to head to the office of the assistant dean of students. Once there I was greeted by the dean and a very somber looking man. I recognized him, but couldn't remember his name at the moment. I sat down and the somber man looked at me with tears in his eyes and told me my parents were dead. He kept talking, but damned if I can remember what was said. All I remember is he told me that a drunk driver ran them down as they were crossing the street and the driver, one Bobby Lance, was currently in jail.

Twelve hours later I was back home planning my parents' funeral, trying to wrap my mind around what was going on. 2 years previously my grandfather had passed, my grandmother having passed a decade before his death, and my father took over the business entirely. Now I guess it was all mine, but I had no interest in it. I wanted to be a mathematician and become a teacher or professor. Anyway, it didn't take long for me to make all the arrangements. My parents were well beloved by the entire town and I had more help than I needed or wanted, but I accepted it graciously. My parents were buried on a Wednesday in adjoining plots. It was a chilly, but sunny, day. As I stood there surrounded by people I barely knew, I silently cried.

The next few days were a blur. I made up my mind to sell off the entire business to a friend of my father's, though he was sort of a business rival. While I know he lowballed me on the offer, he still offered more than he would've to anyone else. In the end, I got just over $75,000 for a business that pulled in that much in alcohol sales every two or three months. Not a lot of money today, but then it was a huge amount. So I had the cash and my parents' house and no idea what to do next.

After about a week I decided to head back to college, but the next bombshell got dropped on me before I could leave. The asshole who ran down my parents had apparently gotten off with a mere slap on the wrist. I seems his daddy was some big shot Chicago politician. He greased enough palms to get junior off. My first reaction was complete and utter shock, then I got angry. Very angry. I'm not very demonstrative, in either anger or love, but when the anger hit, the glass I was holding was flung against the wall. I swore then I would get my revenge one way or the other on him. I took a deep breath and with a heavy heart I closed up the house, knowing I would probably return once I graduated college. I changed majors and switched to business and I'd spend the next few years on learning on how to make my money grow. If it was money that got him free, I figured money will be needed to bring him to justice.

Now it was during those years in college that "blossomed". I still don't know what actually caused me to shift into Mary one night, but I did. I went to bed Tom and woke up as Mary. Now, as Tom, I'm a solid 6'1", about 180 pounds, fairly lean yet muscular, brown tousled hair, deep brown eyes. As Mary, I'm 5'7", around 140 pounds, I have long wavy auburn hair, bright green eyes, very busty (I can somewhat adjust my breast size from 38DD to 40DD, but tend to stay at 38DD), an hourglass figure and long legs. I have no idea what happens to weight when I shift, but it seems to just come and go depending on who I am. I stopped in trying to figure it out a long time ago.

The morning I woke as Mary was a Sunday. By now alcohol was legal again and I have to say really enjoyed myself on the weekends at that point of my life. All I could remember is that I had crazy dreams. Looking back at it now, my subconscious probably knew what changes my body was undergoing and it tried to prepare me. I wasn't prepared in the least.

I rolled out of bed sometime well before dawn to go pee and all of a sudden I was off balance and couldn't figure out why. I let out a squeal as I stumbled in an effort to regain my footing, plopping back down on the bed, and then I realized that my voice was different. I fumbled for the light and turned on the lamp next to my bed. I looked down and saw a massive pair of tits on me and cried out. I stood up and awkwardly rushed to my bathroom to see what the hell had happened. In the mirror I "met" Mary for the first time. I held up my hands and looked to see if this wasn't some sort of trick. It wasn't. I stripped entirely to see just how far the changes went. My dick was gone replaced by a pussy topped with a little tuft of red hair. Of course I touched to make sure and it felt real!

It was at this point I was quite happy that I lived alone since I was renting an apartment off campus. I didn't need a drunken roommate stumbling in seeing a gorgeous naked woman. I walked back into the bedroom and sat down on my bed, trying to figure out just what happened. By this point I was stone cold sober, but still needed to pee. Once again I walked into the bathroom and, out of habit, stood in front of the bowl, but realized quickly I needed to sit down! One question answered for me, the pussy was definitely real. I walked back to the bedroom, again, and my mind was all over the place. This was too fucking weird. How the hell did I go from being a guy to a girl in a few hours? Is this some crazy dream or some bad joke?

I laid down and just tried to figure out just what the hell happened. I was a girl now. But how? I knew the pussy was real because I just peed, but did it work in other ways too? Only one way to find out, so I reached down and kind of fumbled around a bit. As a man, I wasn't a virgin, but I really didn't know how a woman's body worked. After a minute or two, I hit the jackpot and started rubbing on my clit. Yep, very real. I continued with what I was doing and I could feel something was about to happen so I rubbed faster. It didn't take long before I knew I was close to cumming. Of course, at that point I had no idea, this was a first for me, but once it happened, I exploded. As a man, I never really knew what an orgasm was, but as a woman I just had my first. Holy fuck it felt so good.

I laid there panting as waves of pleasure continued to wash over me. I was exhausted by what had just happened and yet still confused. As much as I enjoyed myself, I didn't want to be a girl. Even though I was fucking gorgeous. As I slipped back into the darkness of sleep, I kept thinking to myself that I wanted to be a man again, that I wanted to be me.

3 hours later I awoke and I had a hell of a hangover. But once I remembered what had happened, I immediately sat up in bed. I looked down and saw that I was a man again, but I was different. Prior to my first change, I was a bit chubby. Not fat, but not fit either. Now I was chiseled. One other change that happened was that I went from being a guy with an averaged sized dick to now having one that quite large. If turning into a woman for a short period of time got me a huge dick, I'm OK with that! All I could figure out was that the first change set my body to what I thought was the ideal man, same for the ideal woman. I'm no scientist and I refused to allow myself to be studied, so this was my best guess.

The next few days after my first change, things were normal and I started to convince myself that it was all just a very real dream brought on by way too much alcohol. Boy was I wrong. After my last class on Thursday, I headed back to my place to study and grab a bite to eat. This was 1935, so there was no fast food restaurants or anything like that around, so I had to fend for myself by actually going to the grocery store. Let's just say that things now are a hell of a lot better food-wise than they were then. I was able to grab a couple of apples and some teacakes. I had no refrigeration then, so I bought what would hopefully last me a couple of days. Thankfully there was a diner nearby, so I never starved.

As I walked back to my apartment, I started to think back to Sunday and what happened. I was still trying to convince myself it was just a very real dream. I mean, it was completely ridiculous that I actually changed into a woman! However, what I didn't realize then, all I had to do was want to change and I could. I can control it now, but not then. I was about a block away when I had the thought it would be kind of neat if I could be her again just for a moment. And then I was.

This was the first time I actually felt what the change was like. Imagine standing under a shower and you're being covered entirely in very warm water, the sensation of how your body heats up and how glorious it feels. That's what the change is like, minus the water. I felt my body grow warm and everything sort of shimmered for a second, my vision blurred briefly and all of a sudden my bag felt quite heavy and my clothes felt baggy. I didn't know what happened, but I glanced in a window and I saw. I was a woman again. I nervously looked around to see if anyone had seen what had happened, but no one seemed to be reacting. My reaction, though, was immediate. I ran as fast as I could back to my apartment and hoped I wasn't being chased.

As I rushed inside, I shut the door behind me and locked it, just waiting for the police or someone to start pounding on my door. After a couple of minutes I realized I was safe, no one was chasing me. I sat down and tried to understand what had just happened to me. I wasn't sleeping this time, but I changed! But how??? I was just walking and not doing anything. I racked my brain for a few minutes before it dawned on me I actually thought about being a woman again and it happened. It couldn't be that simple, could it?

So I closed my eyes and thought about how I wanted to be a man again. And nothing. Not that simple. I tried for about 30 minutes and nothing happened. By now I was getting frustrated and began to cry. I sat there and sobbed, begging to whichever deity was listening to change me back. I thought deeply about much I wanted to be a man again. And I felt it. I could feel my body change and my clothes fill out. I got up and went into the bathroom to look in the mirror, I was staring back at me. Not a woman! It was right then I knew I had to get this under control sooner rather than later, otherwise it would cause me a lot of problems.

I skipped my classes the next day and stayed in my apartment. After a few hours, I finally was able to figure out how to change, but I needed to get it under control. That took me the better part of Friday night and Saturday. Eventually, I felt confident enough to show myself in public again without fear of accidentally changing. I had no choice but to go out and get something to eat. I had run out of food and I was starving. I got dressed and headed to the diner. Thankfully it was uneventful, but on the way back I passed by a dress shop and I realized that I would need to get some clothing for the female side of me. Unfortunately the shop was closed and I'd need to wait until Monday. But that also gave me time to practice more and get an idea what size she... I wear.

Monday I was back in school. It was my lightest day, so I was able to head to that dress shop. Again, this was 1935. Women typically wore dresses and stockings then. I was not exactly happy with that idea, but I didn't have much choice. As I entered, I realized I was both nervous and excited. The woman who helped me was quite pleased that a gentleman would take great care in what his lady would wear. I ended up getting a couple of house dresses, a few afternoon dresses (a woman then would never think of leaving the house in a house dress!), a few pairs of shoes, a handbag, and, most surprising of all, a couple of pairs wide bottomed pants and some blouses. I was all set, except for undergarments. A gentleman would never buy such things! I needed to get that figured out.

I headed home with my haul to try everything on. Once alone I allowed myself to change and I got down to seeing how things looked on me. Thankfully most things fit, but I needed different shoes. I'd need to return to the store, which was not the worst thing in the world. The bra would be the hardest thing to get. I was just too busty to go out without a bra. I'd need to wrap up my boobs the best I could and go shopping for one later.

A few days later, after practicing walking in those goddamn shoes, I felt like I could finally go out as Mary. I decided to name myself Mary since it was my mother's name. I changed and got my boobs wrapped and I put on a cute floral dress. I looked in the mirror and I loved how I looked. I also realized then I'd need to learn to do makeup if I was going to continue to lead this double life. Being a man is much easier! I grabbed my handbag, took a deep breath, and walked out into the world for the first time as Mary.

It was oddly exhilarating. The first thing I realized is the hair would be an issue, so I knew I'd need to learn how to do it up in a bun. I liked its length, so cutting it wasn't an option. Knowing I needed to buy more things for Mary, I hailed a taxi to take me to the large department store where I could get some feminine essentials. I spent hours in there. The ladies who assisted me in learning make-up and hair care were a Godsend. I also picked up a few bras and undergarments. They didn't bat an eye when I mentioned that I had lost my family and was starting from scratch.

I should mention at this point that it was then that I realized just how different I was as Mary than I was when I was Tom. As Tom I'm 100% heterosexual. I have absolutely no interest whatsoever in men. As Mary, it was pretty much the opposite. This hit me as I was shopping and the manager came over to see how I was being treated. He was obviously flirting with me and I reciprocated slightly. The attention he paid me affected me physically in that it caused my pussy to get quite damp. It shocked me and I got very shy, very quickly. He noticed and he excused himself so I could continue to shop, but he glanced back and me and smiled, which got me even wetter. I was not expecting to react in such a way.

As I was about to walk out of the store, the manager approached me again to formally introduce himself (his name was Michael) and to ask me how my experience had gone, if I was satisfied with how I was served. I must've blushed as he asked because he smiled softly at me. I let him know that all the ladies were wonderful and that he had an excellent staff. He then asked me if I was free for dinner some evening and I quickly, perhaps a bit too quickly, said I was free any evening. And just like that I had a date on Saturday night, which was the next night. He gave me the address of the restaurant and we made plans to meet there at 7:00. He walked me out of the store, hailed me a taxi, and said he would see me tomorrow.

When I got back to my apartment, I immediately flopped on the bed, spread my legs, and put my hand on my pussy. He had gotten me so aroused in just how he looked at me, that I had to masturbate. It didn't take me long to cum as I thought of his deep voice and piercing brown eyes. I slept quite well that night.

Now I wish I could say that after our date that we went back to his place and we fucked like bunnies, but this was the 1930's. Now while it did happen on occasion for many people, that didn't happen here. No, we had a lovely dinner and he was the perfect gentleman. He walked me home, as the restaurant wasn't too far from where I lived, and made sure I got home safely. We made plans for another date. I thanked him and kissed him chastely on the cheek.

For the next few weeks I lived as Mary when I wasn't going to school as Tom. It was then that I noticed how women were treated as compared to men. Women were not treated well for the most part. They were still thought of as "homemakers", even though many were entering the workforce, albeit at much lower wages as men. If not for such women as Ruth Nichols, Beryl Markham, and Amelia Earhart, who knows how women would've been treated? Unfortunately, it wasn't until 1938 that women had any sort of "women's rights" thanks to the Supreme Court. But I get ahead of myself.

I dated Michael for a short time, but we never went further than that. It turns out that I am "too strong willed", his words, and we parted company. It was during the time I spent with him where I figured out who I was as Mary as compared to Tom. Obviously, sexually speaking, I thought differently, but my personality for the most part was unchanged. I was just as outspoken, I was not quick to anger, and I had a very keen sense of right from wrong. As Mary, I was more flirtatious than as Tom and a bit more shy. Whereas when I was Tom, I tended to be more forthright in my opinions. As Tom I was quite sexually active, though not recently, as Mary I was still a virgin.

November of 1936 changed things though and a decision had to be made. Social Security numbers were introduced and I had to decide which of my identities should get one. I saw the writing on the wall and realized that if I was to work as Mary, I'd need one. As Tom, I knew I'd definitely be getting one. In the end, I got one for each identity on the off chance I decided to live full time as one or the other. I just applied 2 weeks later as Mary. In the long run, especially considering my long life, I didn't need to do that, but one never knows how the future will go.

Fast forward a bit to 1938 and I'm now working as an accountant at an investment banking company in Chicago. Not my ideal plan, but I knew I wanted my money to grow and this was the best place to do it. My plan before the death of my parents was to work as a teacher at a prestigious college of some sort, but that dream died when they did. However, as I worked there, I became friends with numerous traders and they helped me to grow what I had. I took in every bit of knowledge they gave me and I applied it grow my wealth. I took no risks and it paid off. Every paycheck I received I banked and I lived as frugally as I could. The $75,000 I had received after my parents had died had grown to nearly $200,000 by the time 1941 rolled around. I got incredibly lucky because it could have gone horribly wrong.