A New Story Begins!

So, this one is called Alex in Wonderland. Here's the first part! Hope you enjoy and thank you!

It didn’t take long for me to find the place. I’d been focused on it, obsessing over it, for weeks, now. Ever since I saw the ad online, which was a rabbit hole of a different sort. 

I guess I should start by telling you about the one thing I never tell anyone. But for the rest of this to make sense, and that’s a big ‘if,’ you have to know the secret I never shared with another soul. Only a complete stranger and you fine folks. But that’s the way with secrets, isn’t it? As much as they weigh, it is far better to burden a stranger with them. People who often know nothing of us but our secrets, and so, to them, we are that secret.

For me, it was a simple thing, but an impossible one. I liked to feel like a girl. Maybe it was because I’d discovered the old wardrobe in the attic with all of my grandmother’s clothes. Not the ones she wore when I knew her, the flowing red tents adorned by blue and yellow flowers that hid her increasing size. No, these were the things she wore when my father was young, clothes of a fashion long gone, but they were beautiful in my eyes, no matter the age or the aroma of moth balls that accompanied them.

Old stockings made of real silk, dresses that fit easily over the lanky frame of a twelve year old body. And still fit all too well on the body of a fifteen year old. Only by then, I knew it was wrong, and I also knew it stirred something inside me.

Most teenage boys are familiar with the art of self-pleasure by the time they clock twelve or thirteen years on the board. As with any kid, I could get myself to climax in pretty short order, but it was always better when I wore some of the finery. When I felt softer, and not just because of the clothes themselves. Wearing women’s underwear, the trappings of femininity, it made me feel soft and girlish right down to my bones. 

But I wasn’t immune from the talk among my friends in high school, either. I knew what they would say about me, and what they would think of me, if this secret were ever to be shared. I would be an outcast, at best. More likely, the one in their midst that they thought of as the funny guy, their old pal Alex, well, I’d become an object of constant bullying. I’d already drawn a few questions when I announced over lunch one day that I didn’t care much for sports. They chalked it up to my size, which has always been slight, but the nudges and quick asides about me belonging in the kitchen didn’t go unnoticed. Over time, they subsided, and, by the time I graduated high school, the jabs were more nostalgic than pointed. 

But I was that outcast. The part of me that felt so good was the one I could never share with the boys that I called my best friends, and certainly not the girls, who I found attractive both as sexual creatures, and for their fashion, the way they moved and talked and laughed. I wanted them and wanted to be them in equal measure, I think.

And then it was time to leave high school behind. It was easier than I thought it would be to leave my friends in the past along with high school as a whole. I moved away to college, found a little one-room place above a club, and resolved to start life anew. 

The city was bigger than the one I’d grown up in, but not so big that one could possess complete anonymity. I saw the same faces at Rik’s Foodland when I went in for groceries, and the same joggers ran in the park near campus. I didn’t know names, but I knew faces, and they knew mine. I always offered a smile, and so became loose acquaintances with some of them. But never too close to be real friends, nor too distant to share that hidden side of myself.

I hoped I’d left it behind, along with those muggy evenings stolen away inside the attic, but the desire for feminine things wouldn’t leave me. And then I discovered the horrible thing about freedom. If you have no close ties, and no one to tell you no, you can get up to all kinds of strange things on your lonesome. 

I started by ordering a few things online. Some panties, some makeup, even some things to help keep my leg and torso hair in check. Once classes were done and I’d worked my time at the library to keep my grants and all, I’d retire to my little one bedroom, shouldering past a river of bodies on my way home. The apartment I lived in was right on the main street in the city, the one that catered to the college kids. It was a row of fast food places and bars and tattoo parlors and smoothie shops. While the rest of the college gathered there to blow some money on a Friday or Saturday night, I would stalk up the stairs beside the Bourbon Street Bar that led up to my room. There was a floor between the bar itself and my apartment, a space reserved for offices for the raucous blues bar, so even on the weekends it wasn’t the worst of distractions, but it was ever-present. While I was in the shower making sure my legs and chest were smooth and supple, sounds of swinging jazz drifted up and nestled in the background, a low-volume soundtrack to my attempts at feminizing myself. 

As time went on, I got bolder in my purchases. I had several pairs of underwear, enough to get me through the week without male clothing touching my unmentionables. I owned four dresses, some shorts and tees designed for women, two bras, six pairs of shoes, and a single wig of blonde hair. Stereotypical blonde. Sue me. 

The evening routine went like this: 

Step one, shave and makeup. Making my skin as baby-smooth as possible was accomplished with razors, some depilatory cream, and lots of lotion. When I was done with skin care, I moved to makeup. YouTube was a godsend for this. I had to play and experiment, but it didn’t take long before I knew my way around foundation and contouring tricks to give myself an illusion of total femininity. While I would never have the backbone to carry through with it, I felt like I could pass for a girl so long as no one looked too close, and I didn’t have to speak. Even at my most girly, my rather deep voice for my size gave me away in an instant.

Step two, dressing. What was I in the mood for? That was the question that began the sifting through my womanly attire. In addition to the clothes I mentioned before, I had some accessories, too. A couple of belts, a purse, some clip-on jewelry. I never took more time than was necessary, but I didn’t rush, either. With my shaved and oiled skin, my lady outfits felt amazing against my skin. By the time I was fully dressed, I was sure to be hard. Which, of course, led to…

Step three, in which I would park myself in front of my laptop with a bottle of wine handy, fitted with my wig. The picture completed, the drinking commenced. I preferred reds, the sweeter the better. And I especially liked how my lips left prints on the glass from my lipstick as I began my search. And that search would be only the finest of pornography for my female self. I was especially taken with college age girls, close to my own age, and while I could appreciate the more savage offerings, I was a gentle sort. The images of strap-on seductresses taking charge and railing some sweet and innocent thing was arousing, sure, but not my thing.

No, what I wanted was a pair of girls tenderly exploring one another. Long moments of lips meeting and tongues dancing while fingertips first tested, then held, young and firm breasts. In these videos, the girls would start off dressed and then become more and more visible as experimental kissing turned to passionate groping. I imagined myself as one of them, usually the wanton blonde in the video. I was quick to skip without a wanton blonde, I had standards! While the video played, I rubbed myself over my panties until my lust could not be denied any longer. Then and only then would I remove my shaft from its satiny cocoon and take matters into hand, quite literally.

The final step, five, I suppose, if you counted cumming as step four, was the quick closing of my browser window, often with a snapping shut of the laptop lid, and the waves of shame and self-recrimination that followed pampering my girly side. 

It was an awful cycle, but I could neither deny it, nor could I refuse the reflexive anger at myself for feeling these things, and the synchronous distaste for surrendering to the urges and denying them. 

Which brings me to The White Rabbit.