"Sissified": 12 Days of Sissy-mas

Because of her warm, encouraging tone of voice I took it as a compliment, as the dildo went deeper inside me, causing a crazy mixture of adrenaline rush and increasing inner burn. "Thank you, Mistress."

"You're welcome, slut," she responded, another of her constant reminders of what I was becoming.

After another minute, it was all in. I declared with some pride, even as the burning sensation increased from the dildo reaching new depths, "All in, Mistress."

"Good girl. How does it feel?"

"Full. Some pain, but good," I answered, trying to report my feelings as accurately as possible, feeling she was worthy of my complete trust. I'd sometimes read stories about inconsiderate Dommes, and those weren't her: even though we hadn't met face to face (that I knew of), I knew that my Mistress had my back. (Or in this instance, my backside, LOL.)

"All as expected," she said. "Now slowly fuck yourself like the bimbo slut you are. Not too vigorously at first."

"Yes, Mistress," I obeyed, as I began doing just that. It's a surreally strange experience when it isn't your own cock doing the fucking, as my body moved in opposite ways from when I was with a woman.

As I slowly moved back and forth the pain began to fade, and an undeniable pleasure began to increase, as my rock-hard cock swayed back and forth beneath me. "Oh, God," I moaned, wanting my Mistress to know I was beginning to enjoy the sodomy.

"Good girl," she purred. "Is your kawk hard?"

"Very," I moaned, as I began going faster.

"Very soon we'll learn if you're a complete sissy," she predicted.

"How?" I asked, wanting to be one.

"If you come just from getting fucked and without your kawk being touched, that's a sissy orgasm," she explained. "So while you fuck yourself, keep both hands on the floor."

"Oh," I said, as I felt my balls boiling, and wondered if I might indeed come just as she described.

"You're going faster now, aren't you?" she asked. "Just because you want to, yes?"

"Yes," I admitted.

"You really are an advanced sissy," she praised me.

"Thank you," I moaned, as I fucked myself.

"Tell me how it feels to have your pussy stuffed," she ordered.

"So good," I moaned.

"You can do better than that, sissy," she scolded, "talk to me," her tone shifting to slightly annoyed.

"Sorry," I apologized as I rephrased, "I love having my slutty cunt filled with a big fat cock."

"Better," she approved. After a moment, she ordered, "Tell me what you are."

"I'm a slut for big fat cock," I declared with a moan as her questions and my humiliating answers added to the euphoria building inside me.

"Would you rather have a kawk in that cunt of yours, or have your dick in a pussy?"

That was a tough question. The answer should have been obvious. I mean, any man would prefer their dick in a pussy, wouldn't they? Yet, at the moment I wasn't a man, I was a sissy; and the answer for a sissy was equally simple. I replied, giving the answer I felt was truest at the moment, "I'd rather have a cock in my cunt."

"Good answer, sissy," she approved. "You are already understanding who you really are."

I was really fucking myself now, my desire to be a complete sissy consuming me, as well as feeling an indescribable pleasure that was creating pulsations throughout my very core... my cock felt ready to burst without even being touched. Was such a thing even possible?

Wanting her to know I was indeed accepting this part of my inner being, I admitted, "Yes Mistress, I'm a submissive sissy for cock." I then added, following two deep thrusts, "For any cock."

"You have my permission to come if you're able," she offered, seeming to be impressed by my declaration, "but only if you can do so without touching your dick."

"Thank you, Mistress," I moaned, moving much faster now, taking the entire cock in my wanton cunt, desperate to come, wanting nothing more than to experience my first sissy orgasm.

"I can tell that you're close, sissy," she told me.

(Her accurate appraisal likely came from hearing my whimpers, which were a blend of masculine and feminine. In essence I felt I was manifesting a third gender that didn't appear to have a name. 'Neutral' wouldn't work, since my mental and emotional state had nothing to do with the absence of sex. 'Pansexual' was too broad a term. 'Asexual' would be wrong, since I could never reproduce through mitosis like an amoeba. 'Shemale' referred to someone manifesting two physical genders; Perhaps 'intersex'? Although that term had slightly different connotations from what I was experiencing: I had no desire to become an actual woman; my goal, as I was coming to understand it, was to become more like a woman, a goal which appeared to be perfectly within my reach (with sufficient help and guidance), without requiring any hormonal treatments or surgery. I could tell I was becoming less of a real man, but I wasn't becoming a true woman, I was heading somewhere in-between. So I guess the perfect term for my mental and emotional state right now was 'sissy': and long-term, I was well on the way to becoming a bonafide sissy. But back to the action: I was about to come.)

"Yes, Mistress, I've never felt like this before," I admitted, which was again the truth. This was a completely different experience from being the one doing the fucking (although in essence I was still doing the fucking, but I think you get my drift).

"Your mind and soul are transitioning from your wrongfully born manhood to your natural inner feminine side, that has until recently been locked away dying to get out," she explained, which would have seemed absurd a week ago, and yet now it could explain so many of my new and confusing feelings. And it also could explain so many of my confusing desires in the past: to wear panties and pantyhose or scroll through Tumblr sissy gifs, and so forth.

"I can feel that," I admitted, as if even my body were transitioning into an entire new molecular structure: one that was neither masculine or feminine, and yet both at the same time... a hybrid that didn't really make sense on a strictly physical level,, and yet which went a long way towards explaining my feelings at the moment.

"Oh yes," she moaned, which made me wonder if she was pleasuring herself while she instructed me in doing so. "Man is becoming woman. Straight is becoming not bi, but bent. Ken is becoming Kendra."

Her words made complete sense to me, for I could feel my pleasure driving my transition as it consumed me and my balls boiled. "Yes, I'm truly becoming Kendra," I declared.

"Kendra the sissy," she added.

"Yes, Kendra the sissy for cock," I agreed, totally caught up in this transformative experience.

"For any cock," she embellished.

"Yes indeed, for any cock," I moaned, wondering if a real cock would feel even better than this inside me... I imagined it would. The pulsations alone of a cock should enhance the pleasure tenfold, I bet.

"Cock sucking isn't something you do, a cock sucker is who you are," she continued.

"Yes Mistress, I'm a cum hungry cock sucker," I agreed, adding, "taking every load in my mouth or on my face."

"Now come for your Mistress," she ordered. "Show me how special a sissy you are, Kendra."

"Oh yes, Mistress," I moaned, going as fast as I humanly could... taking every last inch inside my slut cunt with each and every thrust, "I want to be a good sissy for you!"

"Good sissy perhaps, but are you a complete sissy?" she pressed, continuing to demean me, as if knowing that by enhancing my humiliation she also enhanced my lust, and her repeatedly calling me a sissy would indeed help to turn me into a sissy (and even a complete sissy)... which at the moment seemed to be an accurate theory, as with every passing moment I became more like the person she said I was.

"Yes, I'm a complete sissy," I agreed again, not really knowing everything a complete sissy might even do (was I already doing it?), but I was so eager to please my Mistress, and I was getting so desperate to come (I'd never needed to come more fervently than I did at this moment) as I threw myself back on the cock over and over as fast as I could, taking it as deep as I could, feeling my balls getting so close to exploding.

"You're a two-hole fuck slut for any man," my Mistress continued her litany.

"Yes, I'm a complete whore for anyone's cock," I agreed, before adding, "especially some huge black cocks."

"Every sissy eventually wants to be used by black kawk," she chuckled, amused.

"I'd love to have a big black cock right now," I said, wishing there was one right here for me to suck, and maybe even to fuck.

"Tomorrow," she promised, making my eyes go wide in astonishment, but I set even that revelation aside for now with my orgasm so fucking close. "Now come, you kawk sucking... cunt taking... SISSY!"

"Fuck!" I screamed, as my cock erupted from the big black cock in my cunt right now, plus my excitement about the prospect of experiencing a big black cock in some fashion tomorrow, and I spewed my load all over the floor.

"Good girl, very good girl," she purred, as my body trembled in release. "That's how to come for your Mistress!"

"I am coming for you," I told her weakly, as cum kept shooting out of me and my entire body shook like Paige's did when she came... fuck, I was becoming more like a girl: this orgasm was way more intense, and substantially longer, than any I'd ever had before. EVER!!!

"Such a good sissy," she purred.

"Thank you, Mistress," I murmured weakly, my entire body now usurped of energy.

"Now don't waste that cum," she added briskly. "Lick it all up."

"Yes, Mistress," I obeyed, as I mindlessly kneeled down, the dildo sliding out of me, then turned around and licked the cum off the laminate floor like a cat licking up milk.

"Good girl," she repeated. "Have a good rest of the day, Kendra. Do whatever you like except come. Tomorrow you begin your advanced training."

"Thank you, Mistress," I said again, as I heard the phone click and she was gone.

I finished off all the cum, stood up, pulled up my panties and pantyhose, and even though it was still early afternoon I went to the bed... onto which I collapsed, and fell into a deep, satisfied sleep a few minutes later.

DAY 7: Monday the 31st

New Year's Eve.

I would be spending the evening with a bunch of friends, as Paige wouldn't return home until Saturday (the twelfth and final day of my sissy training).

I recalled Mistress M promising I would suck someone's cock today... his black cock.

Did I really want that?

When I was horny, I definitely did.

When not... like now... I wasn't so sure.

Like I said, fantasy and reality are two very different things... although the line between them had been blurring considerably during the past week.

I headed downstairs, opened the Day 7 box and found inside a red lipstick, a blonde wig, a black dress, and black heels.

I read the note.

Kendra

We are into the action stage now.

Today you will suck your first living cock.

Today you will swallow your first load directly from the source.

Today you might take your first facial.

At 1PM I will text you the address for a gloryhole.

You will go there.

You will suck at least one cock.

You may choose to suck more, if you wish.

You will swallow the first load.

Of course, you will wear your new dress and heels, and I suggest a pair of black pantyhose. You will finish off the ensemble with the wig and some lipstick. I know you're not experienced with lipstick, but try to apply it as tastefully as you can. You don't want to look like a slut after all, even though you'll be acting like one, lol.

Mistress M

Once again, I was torn.

I could already feel my mouth watering.

Yet everything I'd done up to now wasn't cheating. Wasn't gay.

Taking a toy in your ass didn't make you gay.

Sucking a real cock was both cheating and gay.

Yet, although I'd like to say I fought long and hard over what to do, an hour later I was all dressed up and watching a YouTube video on how to apply lipstick properly.

Panties were on.

Pantyhose were on.

Black dress was on.

Black heels were on.

Lipstick was on.

Wig was on and brushed as attractively as I could manage.

I looked in the mirror.

And I had to admit, I looked kind of hot.

I then shook my head because I'd just seen myself as hot.

I waited impatiently for the text.

When it came, I gasped.

It was in the south district.

The black district.

A district that was adjacent to the one where I taught. A district that even had a few students going to our school (usually the academically advanced ones, as we were a better funded school, or because they were the athletes we wanted).

Again, a mixture of excitement (as promised, my first cock would likely be black) and trepidation (this wasn't an area of town you trespassed into alone, although at one in the afternoon it should be okay).

I went into the garage, removed the wig in case any neighbors saw me, and drove... finding that driving in heels was harder than walking in heels.

I arrived at the location a few minutes early, and received a text.

You're early!

I responded back: How do you know that?

She responded: GPS tracker.

I texted back, as I put my wig on: Oh.

She responded: Go to room three. Your first cock is already waiting.

I responded, adjusting the wig: It is? (Notice we didn't refer to the person, but only to his appendage).

She responded: I made sure your first was one you wanted.

She added: BIG!

She texted again: BLACK!

I responded, finally satisfied with my wig: Thanks!

She replied: Of course! Have fun! Stay as long as you like.

Likely I'll just stay for one.

That's what they all say, but we'll see. Now go and become an official cock sucker!

I replied, as I got out of my car: Right away, Mistress.

I sauntered in, using my sultry feminine walk, trying to look as sexy and girly as possible, but was happy to see the adult store was relatively empty.

I walked to the back, keeping my head down as I passed two black men both in their forties, I estimated.

I found some video rooms and went into room three.

Closed the door.

Saw there was a television playing porn. A stool. A hole in each of two walls... likely accessing rooms two and four.

A moment later a black cock, semi-erect, popped into my room.

This was really happening.

I walked over to it wordlessly.

I moved the stool away.

I knelt like a good sissy.

I took it in my hands.

Somebody groaned, whoever was attached to the other end of my new paramour.

I stroked it.

I stared at it in awe.

I opened my mouth and took it in.

It felt... so... natural. As if this is what had been missing from my life until now.

It felt... so... surreal. I was finally making a fantasy I'd never fathomed becoming a reality, become a reality.

It was... so... stimulating. Feeling this cock hardening in my mouth was the most magical thing ever.

I bobbed slowly, taking in only two inches of the eight-inch shaft (give or take), really worried I might gag if I tried taking it all in too soon, and figuring baby suck steps were necessary. (Baby suck steps.... Hehehe did I just make up a new term for rookie cock suckers? Hey, I was now officially a cock sucker. Hey, why was that so exciting?)

Once it was completely hard, I began bobbing a little faster, taking a little more into my mouth every few bobs.

I wasn't sure how I was doing, but hearing soft groans made me feel I was doing okay at the very least.

It also made me want to get him off... to taste his cum. I realized I couldn't completely depersonalize this cock, there was a living, breathing, person here, who was getting horny and excited because of what I was doing... not just to his cock... but to him.

"Faster, cock sucker," a deep voice, a young voice, ordered me.

I obeyed, bobbing faster... wanting to be a good cock sucker, a good sissy.

I sucked for two, perhaps three minutes, his moans getting louder. I was getting about five inches in before he warned, "Get ready, cock sucker."

I kept bobbing, and was rewarded... and yes, it tasted and felt like a reward... with a sudden gush of cum squirting into my mouth and gliding smoothly down my throat.

Rope after rope was deposited into me... which made me feel so good... which feeling I realized only enhanced the fact I was becoming a sissy.

When he was done, he pulled out and walked away.

He said nothing.

I sat there on my heels... and waited. Mistress M was right: I wanted another cock. I needed another cock.

I waited another minute before I heard a voice from behind me. "Come suck me, faggot."

"Yes, Sir," I responded, as I crawled, literally crawled, the few feet to the other wall and another black cock, even though being called a 'faggot' made me cringe. It was such a derogatory term.

It was completely flaccid, so I took the entire sausage right in my mouth.

I wanted to feel it going from flaccid to hard.

I wanted to be the one who made that happen.

I swirled my tongue around his cock.

I felt it harden in my mouth.

I felt a rush.

Once hard the guy said, "Now get sucking, faggot. I don't have all day."

I smirked as I thought, I do.

I then began bobbing.

This black cock was smaller, seven inches, but so thick now that it was hard, it spread my mouth considerably.

"Take it all, faggot," he demanded,

I took a deep breath and took it all... my nose actually touching his groin.

I held myself in place for a moment until I gagged and backed off.

"Get that fucking mouth back on my dick," the guy demanded.

"Sorry, Sir," I apologized, loving to be told what to do.

"You will be," he threatened.

I resumed sucking his cock, focusing on breathing through my nose, glad I'd practiced doing this with the vibrator yesterday, and taking as much of his cock in as possible.

I wanted to be a good cock sucker.

I wanted to be able to deep throat.

I bobbed for two or three minutes before he grunted and without any other warning, spewed his salty seed into my mouth.

Fuck, I loved the thrill of having a cock shooting in my mouth.

Fuck, I already loved the taste of cum.

Fuck, I wanted more.

When he pulled out, I said, "Thanks."

He chuckled but didn't say anything.

"Over here," a new voice summoned from behind me.

I turned around and a massive black cock, already erect, was calling to my mouth.

I scurried over and took it in my hands as I said, "Your cock is huge, Sir."

"I know," he said, likely hearing that a lot.

"Fucking huge," I repeated, it was easily ten inches long and almost that in diameter, before I took it in my mouth.

The owner of this massive cock was a man of few words as he allowed me to worship his cock for several minutes.

No name calling.

No humiliation.

Just the odd moan or two.

I knew I'd never be able to take all ten inches in my mouth, but I wanted to take as much of it as I possibly could.

For over ten minutes, I sucked.

During that time I got almost eight inches of it in my mouth.

After ten minutes my jaw began to get sore, yet no way was I going to stop sucking.