So does it start this way for all sissies? I have no way of knowing. But for me it was a slow decent, one little step after another. Panties led to stockings, stockings to heels, and before long I was shaving and wearing makeup. It's all part of the transformation, the descent into full submissive sissydom.
Being a sissy is all about feeling feminine. The touch of silk on smooth shaven skin, the look of shapely calves extending from high heeled sandals, stocking tops peeking from under a too short skirt -- such femininity is intoxicating!
But being a sissy isn't only about looking the part, it's about feeling the part too. Every time I dress, I want to feel as much like a woman as I can, and that lone desire is what drives me deeper and deeper still into the web of sissified lust.
While it was orginally a thrill to drive in traffic wearing a mini and heels, it was the promise of pure feminine bliss that drove me to complete the illusion. Wearing panties and stockings under my work clothes went from wildly erotic to woefully inadequate in a number of months, if not weeks. Once I had tasted the devine pleasure of complete transformation, I could not again settle for some mere half-step.
I did, of course, continue to wear panties and stockings every day, but I found it almost unbearable to have to wait so long between business trips. Aside from Sami's occasional road trip, it was only when away and in the privacy of a hotel room that I was able to be my sissy self. I can't overstate how preoccupied I was with planning my next trip, or how nervously anxious I became when the time grew near.
Thankfully, my company did require a significant amount of travel, and I volunteered for every trip possible. I didn't care where, and every trip was the same. I would waste no time once in my hotel room, to strip of my male uglies and reveal the satin sissy underneath. I would sometimes shower and shave, sometimes not, depending on how clean and smooth I already was. But one thing was certain, I would spend every evening, my entire trip, completely made up and dressed like a hot sexy slut!
But even those wonderful nights dressed in satin and lace, decked out in heels and skirt were soon not enough. Once again, I needed more. So, with styled hair and slutty makeup, I started to venture outside of my hotel room each time while away. My first excursions were nothing more than a walk in the hallway, or occasionally a jaunt down the elevator. I can't even express the thrill it gave me to be out in "public" as a woman.
Before long, I extended my little outings to include walking to my car, and even brief drives. I still remember the feeling of that first time I ever walked outside. The cool breeze chilling my stocking covered thighs as it blew up under my short skirt, the entire experience enhanced so by the sound of my heels clicking on the hard pavement, it was all I could do to keep from cumming on the spot and soaking my lace bikini panties.
But being the sissy that I am, as time went on, and my desire to feel feminine grew, it eventually came to a point where mere dressing up and prancing around just wasn't enough. My fantasies took me to places I had never before dreamed of, and in a way that makes total sense now, at some point I started to dream of cock. After all, what completes the feminine illusion more? Guys don't pleasure cock, but woman do, and as a sissy who desperately wanted to feel like a woman, I increasingly became aware of my desire to experience sex like a woman, and stroked my little clitty to many fantastic orgasms while dreaming of hard cock.
The rabbit hole took another deep plunge at this point, and my fantasies soon led to my purchase of several latex cocks. I started sucking them at first and found that I became very aroused just by placing my lips around the large bulbous head. I was mesmerized by the sight of my painted nails wrapped around the simulated man flesh and thrilled by seeing my crimson red lipstick prints on the hard shaft.
Of course, I didn't stop with merely sucking these symbols of raw maleness. No, my cocksucking ways soon led to me raping my own ass with dildoes of ever-increasing size. I would dawn my slutiest outfits and bounce up and down on a hard latex cock until my little sissy clitty would squirt my creamy load all over everything.
My favorite activity was to put my high-heeled feet in the air and fuck my sissy pussy with the biggest plastic cock I could find, while stuffing my throat with another. I would instantly become so aroused by the vulnerable feeling of lying on my back with my legs in the air. Looking up at my bouncing heels, I would pound my sissy ass-pussy until my elevated clit would start shooting streams of hot, milky sissy cum into my hungry slut mouth. 
Yes, I spent many nights alone in hotel rooms across the U.S., dressed like a complete fucking slut, with a plastic cock in my mouth and another filling my sissy ass. 
Each of those nights would end with me crying for my dream intruder to fuck me harder, to make me his bitch, and each make-believe fuck would end with me madly gobbling all of my hot sticky cum I could get.
As you may have guessed, this isn't where it ended. I would soon no longer spend my every feminine experience alone, but then that is another story . . .
Kisses
It's that first orgasm, that first time you allowed yourself to cum while wearing panties -- that's when you dove into the rabbit hole. And once you dive in, you'll never find your way back. Everything from that point on will only take you deeper. You may stop from time to time. You may even feel you've found your way back to being a normal male, but you're just kidding yourself. You're marking time at best. The next time your inner sissy comes out, you'll take off right where you left off. That's just the way it is in a rabbit hole. 
It wasn't long before my lust drove me to make changes that would allow for more. I soon applied for a transfer at work. The new job did pay more, but that wasn't why I applied. The truth is that the position called for a significant amount of travel, and just the thought of all those nights alone in a hotel room made my little dick start oozing precum in my panties.
