tagTranssexuals & CrossdressersCassey’s First Steps

Cassey’s First Steps


***My first attempt at writing, not trying to be a novelist. Just a person wanting to share his/her (LOL) erotic writings. Feedback would be appreciated.***

As the cab rolled away, I turned and stared at the entrance to the club, noticing the bright neon sign "Mystical Misty's" above it.

An overwhelming of mixed feelings filled my mind "Was I ready for this?"

Here I was on a Saturday night in downtown Seattle, at a club known to cater to various gay and lesbian lifestyles. An online friend had recommended the place if I dared to 'step out' for an evening. As I entertained my mixed feelings about taking the first steps into a world unknown, I thought of how my evening began..

After my long day of having to go into the office on a Saturday, I was ready for an enjoyable evening. Like many other weekends, I was envisioning a night of transforming myself into Ms Cassey, the woman I wanted to be. I poured myself a glass of white wine and began putting my outfit together; I felt a sense of sadness as the evening would be spent alone again.

Since my divorce almost 6 months ago, I had not even gone out on a date as a man or a woman. The divorce, even though it was an agreeable one without any ill feelings towards each other, had me questioning my sexual preferences and choice of lifestyles. The confusion left me feeling withdrawn and hesitant on dating as I did not want to even consider another relationship until I found who I really wanted to be.

As the articles of my ensemble came together, a deep desire to take a chance on life rushed through me. I wanted to venture out beyond the safe walls of my home, which Cassey had become a prisoner of. So I quickly logged into 'chat' to see if my sexy gal pal "misty2u" was online. She was, so I began telling her of my plans to take the ultimate step and wanted to know of any suggestions for a first timer. Overjoyed by my courageous decision, she suggested "Mystical Misty's" and proceeded to give me directions. I thanked her, but before logging off, she made me promise to give her all the details and added a "you go girl" double snap.. I just had to giggle at her silliness and the fact that now I knew where her name idea came from.

As I looked at my reflection in the mirror, I began to wonder if I could pull off transforming a Hispanic, 5'9", 155 lbs, brown-eyed, black shoulder-length haired male into a passable sexy woman. After some thought, I realized how silly it was since the club catered to various lifestyles and so many others would also be at their own beginning stages.

So began the ritual of a soothing bath, then shaving any existing body hair. Drying off was followed by applying a lavender lotion leaving my skin feeling smooth to the touch and a nice scent. The feeling and scent brought a sad smile as I remembered my last sexual encounter with my ex-wife, how I still missed running my hands over her body feeling each curve and inhaling her sexy perfume.

Wrapped in a towel, I sat down to paint both my fingers and toe nails a crimson red. Once dried, I plucked my eyebrows to perfection in order to present the most womanly-look ever. With having practiced, I applied my makeup with the right foundation and blush revealing an alluring appearance without a hint of being sluttish..

Okay, maybe a little sluttish. A girl has to have fun, you know?

Since I am naturally tan, I chose darker colors for my eyes and a deep shade of red for my lips. The added touch was my shoulder length hair, blow-dried and set to accent my cheekbones and eyes.

Putting on my sexy outfit was next, beginning with seamed thigh-high stay-up black stockings. Slipping each stocking over my feet and unrolling them slowly up my smooth legs always sent sparks up to my 'clit'. Once the stockings were snugly secured, I pulled up a cute satin V-string thong, black with a sexy red bowtie in the front. I ran my hands all over my tight ass and along the crotch as the feeling of the panties was almost non-existent, like a soft second skin.

A wicked smile appeared across my luscious lips as the thought of someone other than myself could be sliding these off later, this added some difficulty in being able to adjust my 'clit' in between my legs to lessen the bulge. I had chosen a matching black bra with enough cushioned inserts to push my chest up to allow a natural 34B breasts. A quick look in the mirror gave me hopeful feelings that a lucky person would enjoy seeing me in this state of undress.

Next I slipped into a black knot-front curvy jersey dress that had captured my eye at my favorite VS store. I reflected back on how the cute young cashier had a small laughing smile as I told her it was for my wife, unfortunately I don't believe I was convincing enough and the fact that I didn't have a wedding ring on.

As I grabbed my purchases, she said "Hope 'she' enjoys the outfits" as our eyes met and I became embarrassed but relieved at the same time to know my 'secret' was out.

I loved the dress for many reasons such as how it displayed enough 'valley' that would certainly capture a few stares at the right moment; also, its mid-length flowing look would allow the top of my stockings to teasingly show as I spun around the dance floor. As adventurous as I was feeling, I was certain a hint of my sexy thongs would show too.

Lastly, I slipped into a pair of 4" triple-strap Mary Jane black pumps. Since I had already mastered walking in high heels, it was exhilarating going across my wooden floors and watching the dress flow outwardly as I spun around, thinking of the lucky audience enjoying a glimpse of what lay underneath.

Adding the final touches of a matching silver pear-drop lariat necklace and earrings, a few cuff bracelets, and some rings on my fingers completed my evening outfit. Taking a spinning look in the wall mirror, I was very pleased with the reflection as even my 'clit' twitched at the prospect of meeting such a lovely creature.

"She is not the type of prey you are hunting tonight, honey" I answered back to my thoughts. "Or is she???" I laughingly thought to myself.

It had been two hours in preparations and 3 glasses of wine so I decided on being safe as I reached for the phone to call for a cab.

"Oh my god" I said out loud as it had not occurred to me that my voice would have to be good for the entire presentation. Yes, I had practiced before on my evenings home and chatting online, but this was different as even the cab driver has to be convinced. So I decided to match my look and go with a sultry-whispered voice as I nervously dialed the number.

"Yes, ma'am a car will be right over in 20 minutes" the dispatcher said, which put a smile on my face as I hung up the phone.

I gathered a few needed items for my small purse, did a few 'final' touchups as I watched the clock tick towards the inevitable.

Finally at 9pm, a double honk was heard and I reached to open the door that would change my life forever...

"Good evening, ma'am. I have the address and will get you there shortly" the driver said as he held the door open for me.

As he climbed in to begin my journey, he said "hope you don't mind, if I may say, you are looking very pretty tonight. Someone is going to be lucky to have you in their company".

"Thank you" I replied, thinking how so sweet of him to notice.

As we went on the journey to my destination, I kept catching the cab driver stealing glances in the rearview mirror and I blushed on how I was able to grab his attention. He didn't escape the once over I had given him as I climbed into the cab earlier, noticing a somewhat cute gentleman with a bit of ruggedness.

I decided to risk a conversation so I would be more comfortable using my voice on others. It came as a surprised that Tony (an Italian man at that.. how lucky for me!!) was an aspiring artist but drove a cab Saturday to Wednesday, saving Thursday and Fridays for painting and art shows. Being single, he had decided to move here from the east to capture the scenic beauty that North Washington presented; particularly the smaller towns and pinewoods. The more we chatted, the more I began to wonder why some pretty woman had not put her claws in marrying him yet.

As if reading my mind "I have not met the right woman, is why" he said; I smiled, as he knew my wondering question had been answered.

We finally pulled into a parking lot and I was saddened that our journey was over as well as our conversation. Tony jumped out to open my door and as a gentleman, extended his hand to help me out. After paying Tony, the expression on his face caught me by surprised as I followed his stare over my shoulder to the bright neon sign.

"Wow, I just realized that you're...uhhh I mean that you... I didn't know I was bringing you to this club..."

My heart dropped as I understood that he put my outfit and the club name together and now knew my secret. Tony then took a pen out and wrote on the back of a card.

"I'm sorry, please don't misunderstand... you are very pretty, I just didn't realize... but thank you for the chat. I really enjoyed it. Please take my card in case you need a ride home, I wrote my cell number on the back so you won't have to wait so long".

Even though I had somewhat recovered from our discomforts, I took his card. I was both sad that he was uncomfortable with me and happy that he found me pretty.

As the cab rolled away, I turned and stared at the entrance to the club...

To be continued...

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