Standard disclaimers apply.
I'm Madison - Chapter One - Madison's Birthday
It was the day after my divorce, and I stood in my too-empty apartment, thinking of the way my life had turned out. It was only natural, I suppose. Divorce is one of those things that make you take stock of how your life had gone so far. It had been so promising...college, a job, various women, then finally a wife. It was a letdown when we learned we couldn't have children. A letdown? It was a disaster. For a lot of people, no kids in the marriage meant that they could always have fun, enjoy their life. For my wife, it meant there was no point to being married. I don't think she cheated, but one day, she just up and announced it was over and she wanted a divorce, after 10 years of marriage.
I couldn't say I was shocked. After all - we were hardly intimate anymore. She only wanted to fuck when she had a pure, physical need, and I, well, in truth I'd just gone along with what she wanted. After 10 years, I guess I was just plain apathetic. It didn't help that she was a damned prude. Never wanted the lights on. Never wanted oral, giving or receiving. Always sex in 2 positions: missionary or her on top. I was almost 40 anyway. Maybe I was just slowing down.
At any rate, the divorce turned out amiable. With no kids to fight over, we managed to split things fairly evenly. She wanted furniture and kitchen things. I wanted electronics and tools. The rest we split. No one seemed to want the pictures. We each ended up with half.
So as I stood there taking stock of my life, I wasn't sad about the marriage ending. I guess I was sad about the paths I could have taken but didn't. I thought about my career, which was fine. I telecommuted to a job I actually liked. I thought about my family. Now there was some sadness. We had grown apart during my marriage. And to be honest, I didn't really want them back. I thought about friends. Damn - I didn't have many. I thought about my sex life. I had once been so...kinky, I guess. Ready to try anything once, and probably twice.
Maybe that was my greatest dissatisfaction...
For 10 years now I had been wrapped into one all-encompassing relationship, while letting the other ones, important ones, die. For 10 years, to keep my wife happy, I had agreed to trite, repetitive sex, despite the fact that in my heart, I wanted so much more.
I started thinking more about this. I used to love sex! It was wild! I was wild! I'd been the guy who licked things off my girl's body. I'd use toys on them. I let a couple of my girlfriends use their toys on me! I'd even worn their clothes on occasion. I even used to fantasize about being with men! It had been so long since I thought of that.
In fact, when I was a boy, I used to get so excited sneaking into my sister's room and trying on her stuff. I used to have a girl friend who'd even let me wear her clothes. This was a part of me that had lied dormant for so long. Hell, I remembered with a laugh, I used to have a damned fine ass wearing that friend's one piece swim suit. How had I forgotten that part of me?
My mind whirling with these images, I went to the bathroom and looked in the mirror. Well, I wouldn't look good now. Damned near middle age. Overweight. My hair thinner than ever. I was definitely not a looker anymore. In fact, I thought with a grimace, I can see why my wife wouldn't want to fuck me. I stood there, wondering who I was now. Finally, I asked myself in a hushed, hesitant voice: who are you? After a few moments, I answered myself: I don't know.
Turning away from the mirror, I started thinking again. I was focused on what had been, and what had gone wrong. Perhaps I could use this as a fresh start. Maybe instead of worrying about how I looked now, I could think about how I'd like to look in the future. Wasn't that what every self help column, magazine, and TV show always, always said.
I thought more about how much I used to love dressing in women's clothes, and having those toys used on me. I'd never thought of myself as anything other than straight, but those had felt good. And, now that I was being honest with myself, I did like to look at some guys. I did...I realized with a shock. I really did. Celebrities came to mind mostly, but what about that guy at the gym? He sure had a nice body. I realized with another shock that my cock was getting hard.
Maybe there was a side of me that I'd never let out of the cage completely. Maybe I was afraid of being shunned by family and friends. Afraid that strangers would laugh or call me queer. After all - as a southerner being gay or bisexual wasn't exactly the best way to be accepted.
Well, with my family estranged and no friends to speak of, I no longer had that roadblock. And I telecommute. I could move somewhere, anywhere. Maybe somewhere where I could live the life I chose without fear.
There was nothing stopping me. I could actually start a new life as someone else. Be exactly what I wanted to be. I could explore this side of myself, this side I had repressed and hidden from me for so long, afraid of what everyone else thought. Afraid of what I thought of myself.
That was a thought. I could not be afraid of myself!
In that moment, I decided to change. I decided to explore this side of myself, starting now. I knew I could never pass a real woman. I was too tall, 6'4". I knew there were women that tall, but not many. I also had a square face and big hands and feet. So I wasn't going to fool anyone, but did I want to? I mean, I'm not a woman. I couldn't see myself as a transsexual, losing my cock and implanting breasts. I still feel like a man, but a man who's interests had...expanded. And a man who could wear clothes that everyone assumes are for women. At least around the house. And maybe for a few friends. Maybe even out. What's stopping me? I smiled, thinking I could go make friends that wouldn't judge me. I had no idea HOW to meet them, but in that moment of optimism, I knew I could. This was a path I wanted to be on!
First, I wanted a name. A new identity. Fortunately, life had helped there. My name is Taylor Madison. A life of 2 last names, and people assuming 50% of the time that my name was Madison Taylor. It used to piss me off when they called me Madison. Well, now it could be my name. I decided that the first step would be for me to start thinking of myself as Madison Taylor.
I decided to take action immediately, but not too much at once. I left the house and went shopping. First, the grocery store. I loaded up on salads and healthy foods. All my life, I, as Taylor, hated to eat healthy foods, but Madison could love salads.
On the way home, I stopped briefly at an adult video store that carried a few sex toys. Grabbing lubricant, a dildo and anal beads off the shelf, I quickly paid for them and went home.
I put up the groceries quickly, and took my new toys to the bedroom. It had been so long since I was this horny I could barely keep my hands from shaking! My heart was racing and my legs were weak!
I opened the packages and the lube, took my clothes off, got on the bed, and immediately started fingering myself. It felt so good! Why hadn't I done this before? Slowly, I lubed and started inserting the beads. They weren't big, but I felt a shock each time one entered my ass. I started masturbating as I pulled them out the first time, so slowly. Oh, this felt good!
I reinserted the beads, my ass accepting them easier this time. As I did, I started imagining a guy I saw earlier at the adult video store being over me, mounting me. In my mind's eye I was skinnier, and wearing pantyhose. In fact, I looked like a whore in lingerie, thigh high hose, and high heel shoes. I saw myself sucking his cock, taking it up my ass. I came back to the thought of him mounting me. I raised my legs and spread them wide, imagining his hard body positioning itself to take me.
I moaned at the thought, jerked myself harder, and started shooting cum harder than I ever had. It landed on my stomach, my chest. A drop even landed on my chin. I stopped playing with the beads, leaving them halfway out. My legs dropped slowly to the bed, shaking. I trailed a finger through my cum, playing with it. Then I smeared the cum across my stomach and chest, and brought my finger to my face. Smearing some on my cheek and gathering the drop on my chin, I stuck my finger in my mouth, tasting my own cum for the first time.
My mind was spinning as I lay there. Finally, I got up and went to the bathroom mirror again. Again, I saw that I was almost middle aged, overweight, with thinning hair. But I also saw the cum on my body and on my face. And I realized with a laugh, I still had half a string of anal beads hanging out of my ass!
I laughed louder and longer. I knew that I had a lot of work to do, on my body, on my life, but for the first time, maybe ever, I had an idea of what I wanted. I had a path to choose for myself, to take as long as I could. I had a person to be. I looked in the mirror. I asked myself again: Who are you. This time, I answered with a smile: I'm Madison!
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