tagTranssexuals & CrossdressersSissy Crissi Ch. 01

Sissy Crissi Ch. 01


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, so with no complicating expectations, we moved in together.

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 the thigh-high stockings that she always wore. 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, most women find me quite attractive, but my appeal has always been more of a cuteness. Manly I am not. Some would even say I was a bit effeminate, and Erika was one of them.

Erika and I got along great from the start. It was like chemistry, a good mix, not like siblings, and certainly not like lovers, more like best friends. We shared the most personal experiences, fussed over each other, played and teased - boy did Erika 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 reaching out and holding her, from grabbing her fine ass. But that wasn't part of the game. How I longed to worship her pussy, to kiss her lips. I would do anything for her, and she knew it. I wanted to be more than roommates, more than friends. Oh how I wished she would just take me and make me hers. I wished I could be her slave. Damn it, in all honesty, at some level, I wished I could just be Erika.

But alas this was all fantasy. None of it would ever happen. I was who I was, Chris Taylor, a 26 year old guy who not only loved women but loved all things silky and sexy. From my earliest memories, I had always loved the female form, and I thoroughly enjoyed sex with women, but I had to wonder how much they enjoyed it with me. You see, there was something in me that drove me to submission. It was that same urge that beckoned me toward feminization. It would always start with lust, lust for some fucking hot chick like Erika, but it would quickly turn to a desire to be more like them, to be submissive to them. With Erika, whenever she teased and taunted me, I would imagine us as two lesbian lovers, she the dominant and me her eager slave.

Now, Erika had no idea of my fetishes, of my desire to not only be her friend and lover, but to be her devoted 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 creamed all over her white satin and lace, I always replaced everything just the way I found it.

It was about 8 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 too 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 start my Internet shopping, it was all over. I ordered Hussy heels and ankle strap stilettos. I had the start of a nice little collection of wonderfully sexy shoes. Lacy lingerie and stockings were added to my wardrobe every paycheck. I bought skirts and tops, even an expensive set of silicone breast forms. In only a few short months, my desires had filled my closet. I dressed each and every opportunity I had, and I couldn't wait until each weekend, hoping that Erika would be off on another of her erotic escapes.

I had many wonderful weekends, but this one 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 me swoon, to make my little clitty grow hard in my panties. Dressed as Erika, with stocking covered legs, tightly stretched garter, a tight clingy dress and my come-fuck-me heels, I would imagine that I was the hot sexy female, that I was the one pleasuring the big cocked stud. These fantasies filled me with excitement, but as thrilling as they always were, I wanted more.

I was tired of dressing for my eyes only, of playing by myself. I did so love the ritual of getting prepared, but prepared for what. Even the toys had lost much of their allure, their thrill. Not that I had any intention of putting them away. I did enjoy feeling my butt filled, and I couldn't remember the last time I came without a dildo in my mouth, but I was ready for more. I wanted to be treated like a women. I wanted to feel another person's hands on my body, their arms wrapped around me, pressing my breasts against them. 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, with all my being, I just wanted to submit to my desire completely, to be a total 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. My desires had finally outweighed my fears, and I would venture outside this time.

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. Yes, I had my own panties, not many, but somehow wearing Erika's always made things even better. 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 already 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 than that.

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.

I started with nail polish. It was always 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 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 muster. 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 - work, taxes, gas prices... After a few minutes, I was ready to continue my transformation. I slowly walked to my dresser, making sure to minimize how much my little peenie 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 did look 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 stocking covered 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 adept 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, well maybe a bit more than a hint, of blush, I was ready for my Angel Red lipstick. I did so 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 time ever out enfemme. I would, at first, 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 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 admired the soft, smooth, look of my stockings glistening on my thigh. I placed the cigarette in an ashtray, the wine on the table, and reached over my knee to hold my ankle around the delicate red leather strap. I slowly slid my hands up my calf, drinking in the sensual smoothness. Over my knee and along my thigh, I stopped with both hands resting on my lap, fingers outstretched. My bright red nails, perfectly matching my ankle strapped heels, were contrasted against the tightly stretched white of my skirt. The look stirred my female within. I lulled, lost in a state of feminine bliss.

Time seemed to stand still as I admired my look, lavished in the sensation of having breasts, and drank in the floral scent of my perfume. I opened myself and let all of my senses experience the rush of feeling feminine. I finished my first glass of wine and got up to pour another, the bottle intentionally left in the kitchen just for this reason. The walk to the counter provided another aspect to my female revelry. I moved like a cat, slow and smooth, my hips swaying from side to side, my wrists held limply.

The wine swirled in the glass as I poured. Feeling the need for a dose of courage, I downed the red liquid while standing at the counter and then poured another. Standing there, the long stem of the glass pinched loosely between my fingers and thumb, I spoke out loud, "Why yes, you may," as if asked to accept the purchase of a drink. Fortunately, my voice wasn't at all low for a guy, but still, I found it terribly difficult to sound feminine. Maybe I was trying too hard, or just maybe it didn't sound as bad as I thought.

I finished my drink, poured another glass of liquid courage and returned to the table, this time bringing the bottle with me. Another smoke, it tasted good with the wine. I tried to discipline my thoughts to ignore my continued arousal long enough to plan the night ahead. Driving was out, now that I was on my fourth glass of wine. Maybe I could call a cab, but I'd have to walk a ways first -- no it would be better to just slip into the cab. I shouldn't have had so much wine. Hell, at this point, maybe I should just drink another...

I couldn't concentrate. Sitting there, legs crossed, stocking tops 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 - a masterful man with a large cock who would make me his bitch. My head began to spin as my clitty hardened and my thoughts raced. I could see his large cock in front of my face. I imagined it coming to life with my touch, slowly hardening as I fondled and kissed it. I could taste his manhood, his heavenly jism. I closed my eyes, spread my legs, and reached to touch myself.

With my hand under my skirt, the front door swung open. It was Leroy. I quickly pulled my hand from my crotch, pulled down my skirt, crossed my legs, and still tugging at the short hem to try and hide my stockings, starred up at him, like a dear caught in the headlights.

He looked my way immediately upon entering the room and my stomach started to turn. "Who the hell are you and what are you doing here?"

Good, he hadn't recognized me. "My name is Nikki," I said in the most feminine voice I could muster. "I'm a friend of Chris's."

"And where is the little fag?"

"Fag?" I had never done anything to make Leroy think I was gay, had I?

"Chris had to run a couple errands. He said I could wait for him here. That's not a problem, is it?"

"I can leave if you like..."

"No, not a problem. Don't worry your pretty little head about it," Leroy said calmly as he approached the far end of the table.

"So, are you Chris's girl?" Leroy's tone seemed to suggest more than mere small talk. Was he coming on to me? As he moved closer, around the corner of the table, I could plainly see the bulge in his pants. Erika had many times told me about her love making with Leroy, and it was obvious that she had not exaggerated. My mind raced as my eyes fixed on the hulking figure moving toward me. I pictured myself on my knees, servicing his monster cock, on his feeding me all 10 inches, filling my hungry mouth with his yummy treat.

Now standing only a foot away, Leroy towered over me. "So, you like dark meat, Sweetie?"

Oh my god! "Excuse me," was all I could think to say, "I beg your pardon. I'm not that kind of girl."

"Give me a break. You haven't taken your eyes off my cock since I walked in the door."

Leroy leaned down and put his hand on my stocking covered knee, looked me straight in the eyes and pressed the issue, this time in a commanding tone, "Now don't play shy. Tell daddy how much you want his big black cock."

"Oh my god," I thought, and involuntarily, I glanced down at the monster in his pants once again. Oh shit, I was proving him right. I looked away quickly, grasped the seat of the chair with both hands, as if to brace myself, and sat looking down, speechless. I thought to try and get up, but unless that was Leroy's plan, it wasn't going to happen. Was this my fantasy coming true or some kind of nightmare? I was trembling and confused. The situation was actually beginning to scare me.

I shifted in my seat and leaned slightly away from the muscular black stud. The sight of his large hand now resting on my silken thigh got my attention. Starting at his hand, just below my skirt, I looked down to the high-heeled sandals on my stocking covered feet. I felt the strain of my lacy red garter straps pulling across my smooth shaven ass, as I became aware of the wetness beginning to form in my panties from my hardening sissy-clit. I may have been scared, but I was also obviously becoming very aroused.

I could smell his slightly liquored breath as Leroy, in an oddly gentle way took his free hand and placed it under my chin, and gently raised my head, turning my painted face to look at him. Again he looked me in the eyes. His voice was soft, but his words were anything but. "Now listen to me, Sweetie - we both know that there's nothing you want more than this big nigga cock in my pants, so stop playing fucking games, bitch."

Taking his hand from my knee but holding my face to keep his gaze, Leroy reached forward, pulled my grip from the seat and pressed my hand firmly against his bulging manhood.

"Feel it, slut!"

"It's all for you, baby girl."

"You're making daddy all horny, and you damn well better do something about it."

His cock had indeed begun to swell and even semi-hard, it was already much larger than my little sissy dickie. It was easy to see why he was a powerful, manly stud, and I was a pathetic little wannabe slut. I did want his hard cock, and we both knew it. I shuddered at the thought, but still I felt through his pants, grasped his growing shaft, and without conscious thought, licked my bright red lips. That was all the signal Leroy needed.

Releasing my chin and holding my hand firmly against his crotch, Leroy took a step back, pulling me up out of the chair. As I rose, I felt his free hand begin to push down on my shoulder. I briefly tried to resist, but he easily overcame my feeble attempt.

"Don't fight it, bitch - you know where you belong." Now with increased pressure, he forced me down onto my knees. I looked first at the vivid red paint on the nails of my hand, still wrapped around the now hard cock inside his trousers, then down to see my skirt hiked high on my thighs, my stocking tops fully exposed. The wetness between my thighs became increasingly evident as I contemplated my situation. Leroy released his hold on my hand and lifted my chin once again. I looked up to meet his gaze.

Report Story

bysissycrissi© 22 comments/ 163874 views/ 64 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: