My Glorious Transformation Pt. 01

My first stab at erotic literature, let me know what you think! Part one of a serialized fantasy journey into sissy faggotry.

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About ten years ago, I ended a pretty serious, 1-year relationship with a woman I had met while working at a bar. She was this classic beauty: elegant, dirty-blonde hair, thin frame, striking facial features, an amazing ass and set of perky, small tits. I was incredibly attracted to her, but we quarreled constantly. The separation was pretty painless, and the break-up was fairly mutual. Our lives were moving in separate directions, and it was obvious to both of us. But the direction in which mine drifted, neither of us could have ever imagined.

I've always been good with the ladies. By the time I was 26 I had slept with about 100 women, all shapes, colors and sizes. I was known around town as a womanizer and I took pride in the amount of women I had slept with. I had sex with two sisters at the same time once. I fucked one of my former high school teachers and she let me role play like I was still her student. I got a blowjob from my third cousin at a family reunion one year...

What I mean to say is that I had been around the block many times, and with every woman imaginable, but I had a naughty, faggoty little secret: I had always fantasized about being a woman. Not practically, you see - I knew that my frame and features prevented me from ever being as beautiful as I truly desired. But deep inside, I longed for the silky smooth feeling of women's panties clinging tightly to my plump, smooth little ass. I wanted pigtails and short skirts, lollipops and flirting with guys at the club. I dreamed longingly of throbbing, veiny black cocks, of licking them and savoring cum like the sweetest dessert. I, in short, wanted to be a little sissy slut.

And the time had come for me to finally fulfill my fantasy.

You see, this woman that I had just broken up with also had a little secret, although of a different nature. Right before we ended things, she had searched through my web browser. And I don't mean she perused lightly through my history - she did a deep, thorough search of everything I had looked at, downloaded, entered into any search engine... everything. This had always been one of my worst nightmares, because the amount of shameful, humiliating sissy porn I look at was a true repression of mine, something I was basically unwilling to admit to even myself. And she saw it all.

Luckily, she was an open minded mistress, and she was willing to help me rather than spread my shameful secrets.

She called me up a couple of days after we broke up, ostensibly just to shoot the shit. After a while we got to talking about sexual topics when she giggled and said "Come on, you faggot. I know your secret. You can't hide from me."

I was in shock. Nobody had ever found this out about me before. She started to go into detail about what she saw - the gay and sissy porno captions, the mind-control and hypnosis videos, the cum training and BBC porn, the craigslist ads looking for a pretty dick to suck (which I was always too chicken to follow through with)... All of it. She laughed and called me sissy boy and little fag boy and joked about putting me in a cock cage and a collar and leading me around town on a leash with a fox tail butt plug in my ass.

It was so humiliating, but it was turning me on to no end. You could tell by her tone that she was doing this out of love, not hate, and that she wanted to help me accept my true identity and transition into the role of sissy bimbo slut.

And so the transition began.

It started with makeovers. She showed me how to coordinate cute outfits and how to do really slutty makeup. She helped me pick out wigs and skirts and little tiny blouses. My favorite are the little boy short panties, and she agreed that they made my ass look amazing. She helped me shave all the hair off of my body, from my moustache to my asshole to my legs, and she put me on a very specific diet and exercise regimen to help give me a more feminine build. You could tell the difference immediately - once I slimmed down a little bit and accentuated my female features and movements, I was starting to look prettier and prettier every day. We bought pretty smelling perfumes and cute, lacy bras; the whole experience was so titillating. I was finally feeling as beautiful and feminine on the outside as I always had on the inside.

The next step was attitude training, hypnosis and hormone therapy. We started out with classes on how to be feminine, how to walk, talk, hold yourself, gesture with your hands, and everything else. She taught me how to pucker my lips when I locked eyes with a man, twirl my long hair between my fingers, lick my lips and suck on lollipops and other sweet things. She taught me how to look, act, feel and be sexy. It was a lot of fun for me because it was my first opportunity to unleash my bitchy feminine side, and it felt great. i was born to be a brat, and born to beg for male attention. She taught me how to act in the club when you're out with your friends, what kind of accessories to buy. I get excited just reminiscing about it.

The hypnosis was easy, because I had already begun that by watching sissy hypno videos and gifs online. It's basically just the art of learning how to lose yourself in the moment and completely embody everything that if feminine and sissy. I was really good at transitioning into that mental state of being, but my mistress helped me hone my ability and learn how to be constantly hypnotized by masculinity, muscles, dicks and cum, along with everything pretty and glittery and feminine.

Hormone therapy was also very easy. All I had to do was take pills and the sissy in me came out! My hips widened, my back began to arch a little more to accentuate my sissy ass, my body hair became less and less visible and I grew the most perfect little set of perky titties. I was finally feeling like a woman, my outside finally matching what my inside had always been - a sissy, bimbo fuck doll.

Then it was time for cum training. Now, being a good little dumb sissy dick slut, I had already begun the mental portion of this by jacking off to endless amounts of sissy training, cum training and gay hypnosis videos on the internet. I had also been masturbating myself to just before ejaculation so that I could get a little droplet of precum on my finger to taste. I loved the taste, and always wanted more. I remember one of the most amazing orgasms I ever had - I stayed up all night doing coke with a friend, and when he left I used olive oil to masturbate to gay and sissy porn. It felt like I was cumming constantly, and the line between precum and cum began to blur. Finally, when I knew I had cum for real, I lapped up the frothy mixture of precum, olive oil and the hot load in my palm and savored every last drop. It was an amazing moment that occurred a few months before my training began, and I would always remember it as a truly defining moment in my descent into feminized sissydom.

She had me masturbate and eat every load. I was supposed to jack off at least 3 times a day and ALWAYS eat the load. At first I ate it from my hand, but after a while I perfected a technique of bending over and positioning my cock above my mouth so that I could eat it directly from my dripping wet penis (which we now referred to as my little clitty, or my sissydick).

After cum, of course, came the ass training. I loved butt plugs and had used them a lot of times previously, but always the smallest one you can buy. My mistress took me to a local sex shop and we picked out a series of increasingly larger butt plugs. I loved it so much; it was like buying jewelry for my little sissy ass hole. There were rubber ones, glass ones, metal ones with cute little jewels on the end that you wear all day under your panties. We bought a couple with fox and bunny tails, and a couple that vibrated. We also picked up varying sizes of anal beads, lots of lubricant and some regular dildos for me to suck on (in anticipation of the blowjob training that was soon to come).

Then it was time to learn how to flirt. She started inviting male friends over to party; she later revealed to me that she had been fucking them while we dated, sometimes letting them cum inside her and not telling me. I always ate her out before we made love, and I would sometimes notice a delicious but foreign taste... I wonder what it was... We would have them over for dinner and drinks and when things started to get a little tipsy and steamy, she would show me how to tease the boys and get them hard, nibbling on their necks and ears and making their hair stand on end, sending chills down their spines. She showed me how to move in the most feminine ways, how to give lapdances and stripteases. It was truly a revelatory moment in my life. It felt so natural that I couldn't believe I was born a man. All of my masculinity began to fade away in the strong, sensual arms of these macho, buff guys she would invite over. I was a woman. I knew it, I felt it, I wanted it so bad. I couldn't get enough of these drunken teasing sessions, and I wanted to take it to the next step. We would always let it culminate right to the edge of actual sex, and then stop short.

I began to get frustrated.

"Why can't I start? I'm so ready to suck a dick, I just can't wait any longer! Please, mistress. The next time we have a party please, at least let me suckle on the tip of one of their cocks until he comes in my mouth. I need it. I dream about it!" I jumped up and down like a frustrated little girl, my pigtails and juicy, pretty-boy ass bouncing along with me. Every time my skirt lifted you could see my little clitty, dripping precum on the inside of my legs for me scoop up with my finger and eagerly lick.

She just smiled and shook her head. "You're not ready yet, bitch, and how dare you question my training! First we start with the dildos. Then you'll be ready to suck a real man's cock, and learn how to worship it like a god."

And so we began the dildo training. We had purchased some of varying sizes, all black (by my request), and of various different functions - a few that stuck to the wall so I could suck and fuck them, a strap on she could wear, one that actually came (we filled it up with real jizz we had been saving in jars in the fridge. It was a tasty treat). I started small, learning how to lick and tease and kiss the shaft and balls. Then we would move to bigger dildos and she would teach me how to control my gag reflexes. I was deepthroating like a champ in no time - like I said, this all came very naturally to me, sissy faggot that I am. If I was a good sissy, my mistress would lube up her hand and jerk me off until I came on one of the dildos, then let me lick it all off and begin a blowjob session with the fresh taste of my sissy clitty cum in my mouth. If I were bad she would fuck me in the ass raw with the strap on, no lubrication whatsoever.

Now, by this time - as you can imagine - I was completely unrecognizable from my former self. All of my testosterone had faded, my masculinity had long since gone out the window, and my appearance was completely altered. I was a pretty, skinny, hot ass little blonde slut who could make all the straight men turn their heads instantly. My own mistress even got a little jealous because I got more attention than she did. I couldn't believe it! I was hotter than ANY woman I had ever fucked, and it felt better than anything I had ever experienced before in my life. I was finally who I was meant to be. The only thing left for me was the final step - to actually make love to a real man (something I had never been). It took mistress' training to realize that about myself, but once I did I was set free. Completely unchained from all of the repression that had kept me from becoming my true self.

To be continued...