The Sissy Diaries: Caught En-Femme Part 1
By karissa tgirl bratDear Diary,
Okay, like, oh my God - I can't even believe what happened yesterday! I am so totally freaking out right now. I don't even know where to start. It all started around noon or so yesterday. I woke up with the usual "morning-wood" & was feeling super horny. Mom & Dad were both at work and my sister Katey had gone out of town somewhere with her boyfriend Tony. Ever since she turned 18 last summer, our parents had been letting her do whatever she wanted to it seemed! How totally unfair! But anyways, whatever. I knew I would have the house to myself all day & since I had awakened with a massive hard-on, I decided to take advantage of the situation & indulge in my all-time favorite hobby - crossdressing! I can't explain it, but for years now I've been secretly infatuated & intensely aroused by fantasies of being transformed into a totally sexy girl. At first, I began exploring the fantasy by downloading images, video clips, audio clips & text stories - but no matter how turned-on I got & how good it felt jacking off to those fantasies, it wasn't until I actually began crossdressing myself that I started to satisfy those desires.
I had always been into women and before I began to explore these fantasies, I had never found men sexually attractive whatsoever. I wasn't homophobic - I knew a couple guys from school who were openly gay & had no problems with them at all - they were cool guys. But I definitely didn't consider myself gay or even one of those straight-yet-feminine types either. But there is this other part of me - deep within - that sometimes comes out & takes over and when it does, every ounce of masculinity I have inside just completely vanishes & I feel just as feminine & girlie inside as I imagine any "real" chick probably does all the time. It's times like these that I shed my manly persona, my male wardrobe & even my first name as Kevin becomes Karissa (the girlie name I've given myself while en-femme) and I get all dressed-up in the hottest girlie clothes, do my nails & make-up just like a sexy girl would, put on a wig & make my hair look pretty, spray-on lots of yummy perfume & slowly transform myself into a completely sexy & totally slutty lil' sissy girlie girl. And for some reason, when I finally get done transforming into Karissa & I start using my high-pitched girlie voice, wiggling my hips & ass when I walk just like a girl would, crossing my legs like a lady when I sit down & practicing all the other little feminine mannerisms that I had learned - it was usually then when I began fantasizing about being with a man, or even multiple men. It's hard to understand & impossible to explain, but something inside me clicks when I'm completely in the throws of exploring my girlish alter-ego and suddenly I have this intense urge to really be treated like a girl, and at the hands of a strong, manly man. I get so worked-up imagining being watched, whistled-at & pursued, hit-on, kissed & caressed, looked-at with animal-like, testosterone-driven lust and then savagely fucked, used, abused, humiliated & punished by rough, Dominant Men who want to treat e like a total cum-slut prostitute. And yesterday was exactly one of those times.
Anyway, so enough background info - I gotta tell what happened yesterday. It's so fucked up. um.., where was I? Oh yeah, so, I knew the house would be empty for the next several hours at least so I was, like, totally excited about letting Karissa's sexy-ass "out" & spending the day pretending to be a really hot girl. I got out my little "girlie-kit" from under my bed - which consisted of some of the things I liked to use during my feminization: a really cute long blonde wig that I bought from a company on-line, some glue-on acrylic French-manicured nails, a bottle of liquid hair-remover to make my body silky smooth and of course - my toys - a pink vibrator that feels so fucking good deep inside my tight little ass-pussy & a purple dildo that I like to suck-on while the vibrator fucks me. I brought all this stuff with me as I made my way down to my sister's bedroom - which, to me, was like a gold mine of femininity. My sister Katey has so many hot outfits, a ton of make-up, jewelry & perfume, and oh - like a million pairs of really sexy shoes too - not to mention a couple dresser drawers full of frilly panties, bras, pairs of stockings & pantyhose and so on. I loved sneaking into my sister's room when she wasn't home - I was like a kid in a candy store!
Katey just barely graduated high school but while she was there, she was easily one of the hottest girl on campus. She was on the cheerleader squad, she dated a stud from the football team, she always had all the hottest & latest fashions and of course, had all the prettiest & most popular girls in school as her friends. And if you weren't fortunate enough to be considered one of her "friends", then you were probably just one of her many followers. She always had guys drooling over her - I know a lot of my friends used to wanna come over & hangout at my house just so they could maybe catch a glimpse of her at home. I always admired how pretty Katey was and when I began exploring my inner-girl, I tried to emulate her looks, style & characteristics. I envied her for being born a girl & wished I could be, look & feel just like her - and when I browsed through her short sexy skirts, hot pink halter tops, silky pantyhose and the like - I got to make-believe I was her & that all this wonderfully girlie stuff was really mine.
I went through the hair-removal & grooming process quickly, as I was so excited to begin picking out clothes to wear. I browsed through her massive closet of clothes for the perfect outfit & my eyes grew wide as I settled on a really sexy, red plaid, pleated schoolgirl skirt that had a shiny metallic buckle on the side - which was so slutty that my Mom almost made her take it back to Hot Topic in the mall where she got it. It was perfect! I searched for a top to match and eventually picked-out a totally cute, hot-pink, spaghetti-strapped halter-top that read "Babygirl" across the front - in a very girlie & glittery, cursive-style lettering - which went so totally perfect with the hot lil' skirt I picked-out. I dug through her panty-drawer for some black, sheer pantyhose and a pink bra to wear under the shirt. I put on the bra & stuffed it with some rolled-up socks to give myself some lil' titties, then put on the top. I slid the silky pantyhose up each of my legs - loving the feeling of the material rubbing against my hairless legs as I wiggled around to get comfy in them - then I stepped into the skirt & pulled it up. Oh my God, I can't believe how totally sexy I felt - it's just incredible! At that moment, I was in Heaven - Karissa was emerging and I knew I was going to have so much fun being her all day long! I sat down at my sister's little make-up table & put on the blonde wig - teasing & styling it a bit to make it look really pretty - then I began applying make-up to my face. I had been reading a lot on-line about make-up application & had experimented with it a few times in the past, so I knew what I was doing. The last thing I wanted to do was look like some circus clown or something - I wanted everything to be perfect. So, I started with a light beige foundation that matched my complexion well, then moved on to a pink blush for my cheeks. I applied quite a bit of dark blue eyeshadow to the tops of my eyelids to give myself an even sluttier look, then painted my eyelashes with a black mascara brush to give them that pretty, feminine curl. I traced the outsides of my lips with a dark red lipliner pencil then filled in the lips very heavy & thick with a slightly lighter shade of red lipstick that made them fuller & more pouty, then I finished with a few sprays of my sister's favorite perfume: Passion, which I find to be so very erotic. I squeezed the little tube of fingernail glue onto my fingertips then applied the sexy French-manicured acrylic nails one-by-one, then held my hands up to admire how pretty they looked once I was done. As I let them dry, I decided to check out Katey's jewelry box. Since I had already pierced both of my ears & my nose a few years ago, it was a piece of cake to put in a couple of Katey's prettiest, most dangly earrings and a sexy little diamond stud in my nose. I wrapped a sexy studded choker around my neck & slipped on a couple bracelets & rings that I found amongst my sister's collection of wonderful things. I went to her closet and picked out a pair of the sexiest, sluttiest, thigh-high hooker boots I had ever seen - and stepped into them. I couldn't believe my sister had a pair of boots like these! "No way Mom or Dad know about these", I thought. As I zipped up the boots, I walked over to the full-length closet-door mirror and took a look at the finished product. Oh my God - I can't believe I am looking at me! I was staring at a totally sexy girl that every guy I knew would be fighting over and that sexy girl was me - Karissa, the hot lil' sex-kitten with the half "cheerleader-bimbo-brat" image mixed with the style of a "bad-lil'-punk-rocker-girl". I was so turned-on that all I could think about was shoving my vibrator as deep inside me as it would go while I rode it and pretended it was some big, strong, manly man's hard, meaty cock pounding inside me. I decided to play a bit first - before jumping straight into the bed & slamming that toy up my ass-pussy - so I practiced walking around the bedroom like a sexy girl, sat & crossed my legs, pursed my lips & batted my eyelashes as I talked in my quite-impressive girlie-voice - acting-out an imaginary scenario of being hit-on by some stud in a bar.
I continued playing & fantasizing for hours - totally enjoying how wonderful it felt to be Karissa - knowing that my tiny, little penis was so hard & so throbbing inside my pantyhose that I was building-up to one helluva release once I finally did decide to put those toy cocks to work. My penis size had always been a private source of torment for me as a guy - it created a huge lack of confidence and a very low self-esteem for me - knowing that it was much smaller than average, which left me fearing humiliation and rejection from women because of it. As Karissa, however, I felt grateful for that fact - as it was very easy to tuck my little penis back between my legs and the lack of a bulge gave me the smooth appearance of really being a girl. In fact, while en-femme, I don't even think of it as a penis at all - I call it my "clitty" and when I just can't take all the excitement anymore and I know I need to cum bad, I don't even use it to get-off like a guy would. Nope, I just fuck myself with the dildo & vibrator like a real girl would and as soon as I find this certain special spot inside me to keep probing those toys into - before I know it I get this incredible, super-intense wave throughout my body that starts slowly and keeps building-up until I feel the most indescribable sensation of pleasure all over that lasts for what seems like forever - even before and after my little clitty starts gushing out cum everywhere. In my life, believe me, I have jacked-off millions of times as a boy and although it always feels great to cum like that - it's not even remotely close to the way one of those mind-blowing, earth-shattering orgasms feel while I'm laying there with one toy cock in my ass-pussy & the other in my mouth - totally en-femme as the sexy slut Karissa & fantasizing about being roughly gangbanged by a group of horny guys. Sometimes I hear myself scream so loud and in such a high-pitched, girlie voice that I can't even believe that it's me yelling & begging imaginary men to "fuck me harder" and crying-out moans of "yes Daddy" or "oh my God, fuck that pussy, Sir". Usually when I'm done and the orgasmic waves begin to dissipate, I lay there in a puddle of my own cum & sweat - feeling totally satisfied & completely exhausted - as the femininity I had so intensely felt just moments ago slowly starts to fade away, leaving me wanting to shed the whole feminine persona and get back to my regular-self again as quickly as possible. Since I've done this a few times now, I've stopped feeling that horrible, confused embarrassment that I used to when I first started - instead, I now just kinda "switch-off" my feminine-self and turn back into regular-ol' Kevin again without giving it too much thought.
I remember the first few times I explored being Karissa - how I'd freak-out and become ashamed with myself, questioning my sexuality & losing myself in thoughts that I was just some sick freak that no one could ever understand. I would work myself into a state of panic - quickly stripping myself of all the make-up, girlie clothes, perfume, etc. that I had so excitedly applied not too long ago - and feeling a sense of shame & self-disgust as I promised myself that I'd never do it again. I would vow to myself that no matter how hard my feminine alter ego tried to fight her way out in the future - I would resist her and keep my masculine dignity - but it never worked. I learned that I had this other person inside - and when she wanted to emerge, she would & there was nothing I could do to stop it. Eventually, I accepted it & became comfortable with it all and I even began to anticipate it - looking forward to opportunities which would give me a chance to let my sexy-bitch-within out of her cage & explore those awesome feelings of femininity that I soon began to appreciate & come to terms with. These days, after I get all girlified and work myself into a whirlwind of ecstasy, I just giggle & smile at how lucky I actually am to have the unique ability to be a boy who can occasionally experience what it must feel like to be a girl - even if just alone & only within the private seclusion of my own home. Sometimes I even scoop up my puddles of cum with my long, feminine & pretty fingers and lick it up, which kinda perfectly wraps-up the whole experience of acting-out the fantasy of being a slutty, cocksucking, cum-swallowing, sex-princess - since I'm sure I'd be drinking gallons of it everyday if I really was the lil' whore I pretended to be. As I write this I suddenly wonder, "How many times & how many guys have cum in my sister's mouth?"
Anyways - so I'm, like, getting totally off subject again. My bad. So, there I was - dressed & made-up to look like a totally hot, slutty girl - in my schoolgirl skirt, hot pink top, black pantyhose, hooker-boots, stuffed pink bra, blonde wig, heavy & slutty make-up, girlie jewelry, pretty fingernails & smelling like a yummy lil' sex-Goddess - twirling my hair around in my finger like a bimbo brat would & practicing on my high-pitched girlie-voice. I found a pack of my sister's cigarettes on her nightstand. "Oooh, my parents would totally kick Katey's ass if they knew she was still smoking", I thought, as I opened the pack & pulled-out one of the Marlboro Lights with my fingers. I held the cigarette between my pretty fingers like a girl would, with my wrist limp, arm bent & hand by my face - just like I used to see Katey & her friends do it at school or at the bus-stop (I told you I paid close attention to her feminine mannerisms!) I fished around her night-stand drawers for a lighter and found one - then placed the all-white cigarette between my thick, red, full, pursed lips & wrapped them around it tightly as I flicked the lighter and lit it. I took a deep inhale - my cheeks hollowing as I sucked in the smoke - then I pulled the cigarette away with my pretty fingers as I titled my head upwards a little & pursed my lips while I exhaled the sweet smoke into the air. I felt so sexy at that moment - smoking seductively like a sexy, sophisticated woman would - and the mixture of aroma from the cigarette & my yummy perfume smelled intoxicating. I had never felt more like a woman in my life and I quietly wished I could stay this way forever. I had no idea that events were about to unfold that would quite possibly make that wish come true. All I can say is: be careful what you wish for.
I continued to smoke my cigarette as I pressed play on my sister's iPod & started to dance around like a slutty girl to the playlist of sexy songs that Katey had named "Fuck Music". First on was "Sexy Back" by Justin Timberlake, which was followed by Britney's "I'm A Slave 4 U". I wiggled my ass & gave a pretend lap dance to an imaginary guy as I imagined I was a sexy stripper that every guy in the club wanted to fuck the shit out of, hard & fast. I pictured myself making money off my hot body - whether from tips as I danced or as payments for blowjobs or sex in the back. I started playing out a fantasy in my head of being a slutty lil' blonde white girl who had been forced by a group of mean, black thug guys to become their little pimped-out, streetwalking prostitute in the scary back-alleys of some rough, crime-ridden inner-city where hardcore gangstas & rough perverts preyed upon innocent lil' white girls like me. I envisioned that maybe I had been a scared little white boy who got into debt with or somehow pissed-off these thug "niggas" and because of that, I had been kidnapped & forced to transform into a sissy girlie girl who sucks cock & gets fucked for money to slowly pay them back. I thought about being teased & humiliated as they feminized me, then I imagined how they'd treat me like a girl and "break me in" for the first time - roughly fucking & raping me as I screamed for help and begged them to stop while they laughed & told me to "shut the fuck up bitch" as they slapped me, spit on me & used me like a fuck-doll for hours & hours. As I got deep into my hot fantasy, I let my half-smoked cigarette rest in a nearby ashtray for a moment as I started sucking my purple dildo like it was a cock. I pulled down my skirt & pantyhose enough to slowly push the lubed-up, buzzing vibrator deep into my tight lil' ass-pussy - moaning like a bitch in heat as I felt the dick invade me. Once the toy cock was all the way in and I could feel it pulsating deep inside, I pulled back up my skirt & pantyhose - which helped keep the big vibe pushing all the way up into mysterious parts of me that felt so amazing to be stimulated. I picked up my cigarette once again and took a deep drag - loving the feeling of the smoke filling my chest as the pink cock filled my ass-pussy. I blew out the smoke & began sucking on the dildo once again - taking it down my throat like a hungry slut would swallow a real dick & gagging as it started to choke me. As the vibrator inside me kept pounding away at my g-spot inside, I felt an orgasm starting to build and my moans & whimpers got louder while my breathing started to quicken - the feeling was incredible - I knew I was gonna cum so hard and I couldn't wait! The intensity kept building & building and I knew I was close - I laid there and screamed as loud as I could, "Oh my God! Fuck me! Fuck me with your hard cock, my big black Daddy! Fuck me like a little white girl bitch! Fuck my pussy! I'm your little whore!" I was in another realm - one of complete ecstasy - and with the way I was yelling & crying out, it's amazing I even heard the sound of my Father laughing - but I did.
There I was - my Father's only son, dressed-up in his sister's clothes, sucking on a dildo & writhing around on her bed, in her room, with a vibrator jammed all the way up inside me, screaming out to an imaginary group of black guys to "fuck me harder" - even through all the make-up on my face, I'm sure he could see me blushing. I was completely frozen - the dildo had fallen from my mouth & I was laying there totally in shock, beyond embarrassed as my Father looked at me with disgust & judgment while he stood there laughing in disbelief at what he had discovered. The only other sound in the room was the buzzing of the vibrator inside me - which just made me cringe even more. I reached my hand into the back of my skirt & pantyhose to pull it out and turn it off - hoping my Dad would be kind enough to at least give me a minute to compose myself before he killed me, but he didn't. He just stood there and watched me pull out the toy cock from my ass with this look of utter shame & disappointment in his eyes - but even though, he still had a bizarre look of sick amusement on his face at the same time. It was almost as if he was horrified by the situation but still somehow enjoying the fact that it was humiliating me beyond any kind of description. I had never, in a million years, expected him to catch me like this - but I guess I expected that if he had, that his reaction would have been one of anger & rage. I didn't understand the looks he was giving me & my mind raced with stupid ideas of ways I could try to explain this to be anything other than what it was - but I knew there was nothing I could ever say to get myself out of this one. I tried to speak but when my mouth opened, all I could think about was that my lips were painted red and any words that I spoke would only draw even more attention to that fact and so I couldn't say a word. What could I say? I just waited for him to say something instead.
- To be continued...