Friday, December 18, 2009

Down the Rabbit Hole

Continued from "Accepting My Inner Sissy"

The die was cast. Though I did not yet realize it, my journey to complete and total faggot sissydom was well on its way. As I look back, I often think of that first time I shaved my legs as the real beginning, but I guess at some level, I really know that it all began the instant I first pulled a pair of panties over my little cock and felt the arousal of feminine satin.

Those pretty red panties marked the entrance to my personal rabbit hole. It must be the same for all sissies. That first little hint of satin and lace -- your cock starts to harden without being touched. You run your fingers over your hardening manhood, feeling it through the tightly stretched feminine fabric. Your heart starts to beat a little faster. Your breath begins a shallow gasping. Before you know it, without even thinking, you're stroking your fully hard cock. Moments later you've errupted, spewing creamy cum from your little cock like never before!

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.

Personally, my journey started slowly, but once I discovered Internet shopping and felt the sheer joy of smooth shaven legs, I plunged deep in the hole with wreckless abandon. I did thoroughly enjoy each and every one of those days at work, all dressed in feminine finery under my male work clothes, but the funny thing about rabbit holes is that you always slip deeper and deeper.

It didn't take long before the thrill of wearing panties and stockings hidden under my work suit just wasn't enough. Sami did travel quite a bit, but not nearly often enough to satisfy my desire. I desperately needed to feel more and more feminine, and to do so as frequently as I could.

I began to take every possible opportunity to do the things I couldn't do at work. I would keep strappy "come fuck me" heels in my car, pulling my slacks up to my knees and slipping my stocking covered feet into the delicate leather for my drive to and from work. Soon, I was completely removing my slacks for the drive, sitting in traffic wearing tight clingy miniskirts, my brightly painted toenails showing through the sheer nylon, my silken legs glistening in the morning sun. Those commutes were sublime, and the nervous rush of the big rig truckers who occasionally honked their horns was a thrill!

But as thrilling as it was, feeling completely feminine from only the waist down just wasn't enough. My desire to wear makeup, to style my hair, to paint my nails, to just be able to walk around and see myself primp and prance, was far too strong for half measures. I needed more. My waking hours became a of blur of sissified lust, always focused on the next time I'd be able to doll my face and paint my lips, to adorn my legs with silk stockings and slip my feet into some 4 inch pumps. Only when dressed like a slut, with my cock tucked between my legs did I feel truly alive.
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.

Business travel is such a blessing for a sissy. Checking into the hotel, knowing that you'll soon be in the private sanctuary of your room. Setting your bags down next to the bed, looking in the mirror and anticipating the hot, sultry female who will soon be looking back.

I can't even begin to count the number of nights I spent in those hotels rooms, the number of times I stripped off my ugly male clothing and transformed myself into an attractive, yet always slightly slutty woman.

Each evening began the same. I would restrain myself from stripping immediately, just long enough to call Sami and let her know that I had arrived safely. For some reason, I couldn't bear to call her once adorned in my frillies. But our conversations were never long. As can be expected, I was always very anixious to get my evening started, and as I would find out later, so was Sami.

Once off the phone, I wasted no time removing my horrid outer clothing. It was always so sensual, dropping my slacks to expose my stocking encased thighs, pulling my shirt up to see the delicate lace panel on my panties. I felt such release as I peeled off my shirt and gently carressed my satin covered chest. I would always rush to put on my heels. Fastening the thin straps around my silken ankles, I could finally relax. Sitting in the hotel room chair, I would pull the band holding my ponytail, shake my hair free, cross my legs and take a deep breath. I was home. I was me.

My evenings would proceed slowly from that point on. For me, heels and stockings are the essence of feeling girly, and once I was there, I wanted to relish every moment. I would stuff my bra and then always take my time doing my makeup, carefully applying foundation, curling my lashes, luciously coating them with wonderful mascara. From time to time, I'd pause to move about the room, to pose and take in my feminine beauty. I do so love the look of a semi-hard cock peeking out between stocking covered legs. Returning to my preparations, curling and teasing my hair into the most provacatively slutty styles I could devise, painting my nails or applying long false ones -- only another sissy can truly understand the sheer delight of feminization.

Made up and feeling sexy, I would complete my transformation with a tight fitting mini, one that would acentuate my firm curvy ass, and a blouse to match. A necklace, earrings, bracelets and rings, a mist of perfume, and I was ready for the crowning glory. To this day, I still wait until last to feel the utter joy of wearing lipstick. For nothing says feminine in quite the way as slick painted lips, and nothing says sissy slut like bright red lipstick.

Needless to say, each and every one of those nights ended with this little sissy shooting her creamy cummy load in a mind boggling frenzy of feminized climax. Each shuttering orgasm fulfilled my desires with a wonderful completion, but even as the spasms subsided and the hot cummy spurts turned to a slow creamy oozing, I knew that I was slipping still further into that rabbit hole.

My later experiences would prove this to be true.



  1. I think we all eventually begin slipping into that rabbit hole. Thanks for posting!

  2. Wow, that is so much like my own experience. Thanks for sharing this with us!

  3. I love the story I also love to wear girly things like pantyhose and heels and makeup nad stuff

  4. I would love to meet you sometime and me and you dress together maybe I could wear some of your stuff

  5. Well Anony, my dear,
    You're going to have to show up and not remain anonymous if you ever want to do anything about being a slutty little sissy.


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