Sissy Crissi Ch. 01
Keywords: Crissi, Ch., 01, Sissy,
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*Chapter 1: One Dreamy Night*
Like most Friday nights, my roommate Erika would be gone tonight. She and her new boyfriend, Leroy, were taking off for a private weekend. Erika and I had met about two years prior, when we were introduced by a mutual friend. Being fresh off a divorce, I was in need of a place to stay, and Erika was in need of someone to help with expenses. The match was perfect, with no complicating expectations.
I did enjoy living with Erika. She was a truly gorgeous female, only around 5'5", but with long shapely legs, a full round bottom, and perfectly proportionate breasts. Erika was a fox by anybody's definition. She was as sexy as they come, and she knew it. Part of a lost breed of women, Erika didn't believe in being "comfortable." Her daily attire always included a too-short skirt that accented her awesome ass and showed just a hint of her stocking tops. From her strappy heels to her flowing black hair, Erika was all women - hot, sexy, and confident.
I guess, in all honesty, I was very much attracted to Erika from the day we met. How could I not be? But alas, Erika was prone to dating only the most hunky of men, mostly guys who looked like football players, tall, muscular, and well - manly. Though I've always been fit and trim, I was not even in the same league. It's not that I'm not good looking. In fact, many women did find me quite attractive, but my appeal was always more of a cuteness. Manly I was not. Some would even say I was a bit effeminate, and Erika was one of them.
Erika and I always got along great, but she did like to tease me. Her favorite game was to stand erotically close to me while I was seated at our dining table. She would coax me into turning my chair and then stand straddling my leg. She would press her yummy breasts against me, with her deep cleavage right in front of my face. It was all I could do to keep from grabbing them, from grabbing her fine ass. But that wasn't part of the game. How I wished she would just take me and make me hers. How I longed to worship her pussy, to be her slave. Damn, how I wished I could just be Erika.
But none of that would ever happen. I was who I was, Chris Taylor, a 30 year old guy who loved all things silky and sexy. Erika had no idea of my fetishes, of my desire to not only be her friend and lover, but to be her sissy slave. I had many times visited her panty drawer and played dress-up with her delicate underthings, and with the exception of that one time when I couldn't get my little dickie out of her panties fast enough, and I creamed all over her white satin and lace, I always replaced everything just how I found it.
It was about 6 months ago when I advanced to secretly shaving my body hair, wearing her skirts and tops, and prancing around and pretending to be her. Of course her wonderful set of tall, strappy, open-toe heels were far to small to fit me, but being only 5'7" myself and rather slim, most everything else fit like a glove, a very tight sensuous glove. Once I gathered the courage to order some Hussy heels and ankle strap stilettos online, it was all over. I couldn't wait each week, hoping that Erika would be off on another of her erotic weekends.
But this weekend was different. Along with my wardrobe, my fantasies had also grown. When I thought of Erika with one of her muscular hunks, I inevitably thought about her pleasing her stud, sucking his hard cock, begging him to fuck her juicy cunt - to burry his meat inside her and fill her with his manly seed. Just the thought was enough to make my little clitty grow hard in my panties. But dressed as Erika, with stocking covered legs, tightly stretched garter, a tight clingy dress and my come-fuck-me heels - I wanted more. I wanted it all. I wanted to be treated like a women. I wanted to make a man hard, to feel his cock grow in my mouth. I wanted to be filled with hot salty jism. Damn, I wanted to be a brazen slut.
So, it was finally Friday, and with cock in mind, I said goodbye to Erika and Leroy, and before they were out of our building, I was in the bath getting ready for my own erotic weekend.
After a quick bath and a light shave, I dried and began my preparations. I first tucked my little clitty between my smooth shaven thighs and pulled a pair of Erika's red satin panties up around my girlish ass. I let my long brown locks down from my usual ponytail, brushed out the nasty tangles, shook my head from side to side, and let my hair fall delicately over my shoulders. I was already entering into a lustful bliss as I fastened the lace trimmed garter around my smallish waist, bunched my suntan colored stockings, and began to work them up my soft smooth legs.
All those familiar sensations quickly returned as I tugged the stockings and stretched the garter straps to hold them high on my thighs, just below the gentle curve of my rounded ass. I was starting to feel so completely feminine. I just loved the feeling of silk and satin, and stockings were absolutely the most erotic of feminine underthings.
I crossed my legs, admiring my girlish figure in the dressing mirror, and slowly reached for my Hussies. My hands now shaking, it was difficult to buckle the straps around my ankles, but once done, the look was stunning. A slow, sexy, walk and another look in the full- length mirror and it immediately became all but impossible for me to continue. My little cockette was now beginning to press hard against its silky confines. My first thought was to pull her out and relieve myself, but I wanted my next orgasm to be much more.
I turned my attention to the closet where I pulled out one of Erika's short flimsy dressing robes. I chose the white one, which was a bit plain, with three-quarter length arms and a modest amount of lace along the hem and neckline. Tying it securely around my waist, I sat back down to get on with my business. Crossing my legs in distinctly feminine style, with my feet tucked back under my lap just a bit, I leaned forward and pulled myself to the mirror.
Putting on my nail polish was one of my very favorite rituals. The scent, the bright colors, it all just shouted female. I had always been so jealous growing up. Girls always got all the pretty things, all the smooth and sexy things, the polish, the makeup, the silk, satin and lace, and somehow the scent of polish brought all those sensations into my mind. I picked the brightest red polish I could find. I wanted the most whoreish look I could get. Taking a deep breath, I tried to calm myself and started brushing the crimson paint on my pinkie, but before I could finish a single nail, I had to stop. The feel of the stockings, the electricity that pulsed from my breasts to the tip of my clit was just too much. I felt like I was going to wet myself before I even got dressed.
I quickly uncrossed and spread my legs, and tried to think of things not erotic, things not feminine. After a few minutes, I was ready to continue my transformation. I slowly walked to my dresser, making sure to minimize how much my clitty rubbed between my legs. I took out my favorite red satin and lace bra and fastened it around my tummy. Pulling it up around my small male titties, I adjusted it into place, then reached for my silicone breast forms and filled out the C-size cups.
Another look in the mirror and wow! Oh my goodness, I wanted to fuck myself! I was looking at a sexy young, well-built woman, dressed in her sexy underthings. From the 5" red patent leather heels to my long brown hair gently swept half over one eye, I looked hot.
I eagerly returned to the vanity to finish my preparation. Fifteen minutes later, I finished painting my nails. After a short bit of admiring my handiwork, stretching my arms and fanning my fingers, setting the brilliant red tips spread on my stockinged thighs, I was again ready to continue. Makeup was next, so I returned to enhancing my look. I had been playing with makeup for some time now, and had become rather good at it. I started with my eyes, curled lashes, mine were unusually long, mascara and liner. Next came a slightly heavy application of light and darker blue shadow. After a light foundation, some hider, and just a hint of blush, I was ready for my Angel Red lipstick. I did love everything about lipstick - the look, the taste, the telltale traces.
Another walk to the dressing mirror, this time fully enjoying the sensations between my legs as a minced across the floor, one foot in front of the other - I stood in front of my reflection and struck pose after pose, each that of a beautifully sexy woman. I was now ready to complete my transformation and enjoy my first ever time out in femme. I would try to avoid any close contact, but I so wanted to just walk down a street, to feel the cool evening air under my skirt, to maybe turn a head or two.
I hurried back to the dressing table where I started curling my hair, not too much, just enough to get that distinctly feminine look. A white ribbon choker, long drop pearl earrings, and a quick spray of my favorite Erika scent, and I was ready to dress.
I chose a too tight, too short, very clingy white cotton stretch skirt and a blousy short sleeve button top of matching color. With the buttons opened one too far and the large collar turned slightly up in back, I chose a wide red belt and buckled it around my waist. A bracelet to match my dangling drop-pearl earrings, and I was ready and eager to find what the night would bring.
I readied my purse, placed my coat over the back of the couch, and sat down for a glass of wine and a cigarette to calm my nerves before leaving. I was shaking with anticipation as I took my first sip. The bright red lipstick, first on my wine glass and then on my cigarette, was a reminder of my sluttish look. I crossed my legs and lost myself in a state of feminine bliss.
Sitting there, legs crossed, stockings peaking out from under the tight fitting skirt, gazing at the strappy heels at the end of my soft feminine legs, I began to imagine my strong lover.
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Keywords: Crissi, Ch., 01, Sissy,