"Sissified": 12 Days of Sissy-mas

I admired my nylon-clad legs and smirked.

If that meant you were a sissy, then I was definitely a sissy.

I scrolled through more and more of them until I couldn't last another moment. I pulled my cock out, stroked it for no more than a dozen seconds, and spewed right into the shot glass. Before I even had time to think, I raised the glass and downed the cum before licking the glass clean.

It was warmer than I imagined... it had never occurred to me what temperature it might be.

It was gooey and slightly salty as it slid down my throat.

And as soon as I was done... my question was, What would it taste like shooting right out of a cock?

Fuck!

I really was losing it.

DAY 4: Friday the 28^th

Just like the past couple of days, I went straight downstairs and opened the next box, this time nude except for my panties and pantyhose.

This time I found a pair of 5-inch open-toed heels.

Red.

I bet you're craving cum.

Yep!

Today whenever you're at home, you're to wear the heels. A minimum of four hours today. Practice walking in them. Watch the YouTube clip called: "How to Walk in Heels | Step By Step ★ Glam.com".

Also, I expect you to scroll through Tumblr (for at least an hour) by searching 'Sissy Rulebook'. You will save your favourite 12 rules into a file called 'Sissy Training' and then email them to me at .

As usual, no coming.

Mistress M

Curious and still wearing the panties and pantyhose from last night, since sleeping in the hosiery felt, as I mentioned before, comforting and sensual and natural, I slipped into the heels.

And would have fallen on my face if it weren't for the kitchen table.

How the fuck can women even walk in these with their feet at such an extreme angle?

How do they balance themselves, especially if they have big tits?

I took them off and carried them upstairs to my room. I grabbed my laptop, got onto the bed, put the heels back on, and searched for the Sissy Rulebook.

I then spent a couple of hours scrolling through the impressive account, always being a fan of lists.

I won't quote every number, just the ones I saved and sent to my mystery Mistress (I have a Mistress? Still a rather surreal concept).

#3 A sissy loves cum (a cute brunette on her knees with her tongue extended and full of cum).

I'm not going to lie... the idea of being on my knees in front of a big cock and tasting cum was becoming more and more intriguing... especially after tasting my own yesterday. Before these 12 days began, it had been simply a curiosity and nothing more... nothing I would ever seriously try... yet.

#4 A sissy loves cock (a close-up of a chubby blonde with a fat cock stretching her mouth).

I have a decent cock. Six inches. Yet I'd be lying if I said I wasn't intrigued by bigger cocks... thicker cocks. I couldn't explain it, but it's probably very much like women who want bigger tits or a tighter ass or whatever they think they don't have.

#5 A sissy takes it in the ass (a big tittied brunette in thigh highs pounding another girl in the ass with a strap-on).

It was weird how these photos and gifs worked. They used women to enhance the imagery, yet slyly manipulated men into imagining we were the ones on our knees sucking cock, or this time taking it in the ass.

Not going to lie... the idea of taking it in the ass hadn't ever turned me on before. Yet for the first time I was curious. The girl seemed to be enjoying it... and I know that men can achieve prostate orgasms.... Yet taking it in the ass is definitely gay. Although... Would that be true if it was from a woman wearing a strap-on? Would Paige wear a strap-on for me? Would Paige fuck me? We'd joked about it a bit, but would I want that for real? Fuck, I'm only five rules in, and already I'm wishing for things I haven't ever seriously considered before.

#8 A sissy dresses like a slut (a hot redhead dressed in a schoolgirl uniform posing commando on her hands and knees, her butt closest to the camera and looking back over her shoulder as if she's begging for a big hard cock in one of her holes... whichever hole you like).

I'd kind of cross dressed before... I was doing so now... but only in panties and pantyhose. I hadn't ever considered wearing a completely feminine outfit... although as I lay on my bed in panties, stockings and heels, I realized the only additional garment I needed was a dress. Deciding why not, I got up, almost killed myself again in my heels, and cautiously staggered over to Paige's closet. I looked through her dresses and chose a black one that I recalled her saying was too big for her.

I pulled it on over my head and looked in the mirror.

A wig and some fake tits, and I could perhaps pass as a girl.

Fuck! What am I thinking?

It was one thing to wear panties and pantyhose, but to become completely feminized was a whole new concept.

I shook my head, but oddly I kept the dress on as I returned to the bed, stumbling once, and resumed scrolling through Tumblr.

#10 A sissy loves facials (a pigtailed blonde coated in at least two loads of cum).

I'd only ever given one facial, and I'd felt guilty afterwards because I felt it was too demeaning for the recipient. Even though she'd begged for it. On the other hand I'm not going to lie, a girl with cum on her face looks pretty hot. I hadn't ever considered being on the receiving end of one, but now I wondered what it would feel like... oddly, during these first few days, the demeaning humiliation I'd often felt was a strange turn-on I couldn't explain.

#14 A sissy is a pro cocksucker (a blonde with a big cock in her mouth bobbing furiously as if her life depended on it).

I laughed. If you aspired to being a sissy, you'd better be a cock sucker. It made me wonder what abilities qualified a sissy as a pro cock sucker.

Deep throating?

Not gagging?

Speed?

Passion?

Eagerness?

Swallowing?

I also wondered as the gif replayed over and over, what it would be like to have one in my mouth. This blonde made it look appealing as fuck.

#16 A sissy belongs on her knees (a blonde on her knees smiling with a big black cock right in front of her face).

This one seemed logical, and it seemed to be one of the fundamental truths portrayed in these photos and moving vignettes. The sissy was always either on her (his?) knees sucking, or on all fours getting fucked.

The natural submissive hierarchy intrigued me. Being on your knees looking up at a man was the ultimate declaration of knowing your place.

#18 Sissies swallow (a gif of a cock spewing endlessly into a wide-open mouth).

This one also seemed logical. If you were going to do all the work, you may as well get the reward. Did I just call cum a reward? Fuck!

#20 A sissy will fuck anywhere (a blonde kneeling on a city sidewalk with a cock in her mouth while other people walk by, some of them aghast).

This was the first one that made me really wonder. Would a true sissy really fuck and suck anywhere? I would think a sissy would want to keep this side of her (him?) a secret. I mean it's one thing to fantasize about this stuff, but another to do it. Equally, it's one thing to suck a cock, and a completely other thing to do it in public. Would a sissy's lust for cock and cum override dignity and propriety? If so, shit was that scary.

#23 Cum is your reward (a close-up of a smiling brunette with a nice creamy load all over her face as she scoops it off her chin and eats it).

Did I just call that cum nice and creamy?

Cum as a reward... ha! I just called it that.

God, I can't help but admit I crave sucking a cock... tasting cum.

#25 You prefer BIG BLACK DICK (a hot redhead on her knees with a thick, black cock in her hand with a look of both shock and lust).

Although race didn't completely factor into my growing curiosity about sucking a cock, I would be lying if I denied the idea of a black cock certainly enhanced the imagery, and also my stimulation.

#26 Sissies love garters and stockings (a girl in a black garter and stockings giving a foot job to a nice hard cock).

I had never worn a garter before, but I did love stockings, so I was certain that this too, was true.

The idea of a nylon foot job was also rather intriguing. I bet it would feel really nice. Getting one I mean... not giving one.

#27: Sissies love a good gloryhole (a chubby redhead sucking a cock through a glory hole).

I had never been to one. Truth be told, I imagined they were mostly a fairy tale. The idea of getting a blow job from an anonymous person was rather intriguing. As my desire to suck grew, I wondered if there were any glory holes in my town.

Curious, I opened another tab and searched for them.

I gasped.

There were five of them within just an hour's drive.

One of them was only ten minutes away at an adult store I'd once been to for a bachelor party gift.

Tempting... very tempting.

#28: A sissy loves the taste of her own cum (a close-up of a girl pouring cum into her mouth from a cup).

After yesterday, this was hard to argue against.

#33: Sissies love heels (an otherwise naked girl posing in red high heels and tan pantyhose).

I wasn't sure I loved heels... so far I was finding them quite awkward. Yet visually, they did help to enhance the ensemble I was wearing. Awkwardness aside, I thought I looked great in them.

Fuck, did I just describe my clothes as an ensemble?

#48: Sissies don't decide things. Sissies do as they're told (a girl on her knees begging for cock).

It was weird. Truth was, this entire variety of kink seemed fucked up. Truth was, I was only going along with this indoctrination (for want of a better word) just out of curiosity (which I realize was tough to prove when I took in my hairless body). Yet, here I was on Day Three, doing very little thinking and doing exactly what I was told, without even someone around to enforce the requirements placed upon me.

Maybe deep down I'm a sissy, or at least a sissy wannabe.

Fuck!

This should have scared me, but with my cock hard and my legs swathed in silk, I resumed scrolling through pictures and gifs that drew me deeper into a place I wasn't sure I wanted to go... yet was also not sure I could resist.

#50: Sissies love to be degraded (a girl getting slapped in the face by a big, fat cock).

I couldn't deny it. The degradation thing was turning me on.

I couldn't explain it. I mean, I'd always seen myself as a man's man: I worked out, I played sports, etc. Yet cross dressing, getting shaved and even waxed, plus this endless fantasizing about sucking cock, had awakened a side of me I hadn't known existed. A side of me that wanted to please; one that was very drawn to the idea of being a sissy, a cock sucker.

#51: Big black cock is a delicacy and should be treated as such (a MILF stroking a massive big, black cock with an undeniable look of lust).

The term 'delicacy' should have been absurd, yet it seemed appropriate as I stared at the tantalizing cock.

Did I just call it tantalizing?

Fuck!

Yet I couldn't deny it, there was something particularly appealing about a black cock. Maybe it was the colour. Maybe it was the taboo racial aspect. Maybe it was the myth about all blacks having cocks like stallions. Maybe it was the growing tide of interracial porn.

Likely it was all the above.

But God, the idea of sucking a black cock was all I could think about. I also felt a bit inferior as I stared at this massive cock, knowing Paige's last boyfriend had been a black basketball player. Did he have a massive cock? Was his bigger than mine?

Fuck!

#63: You're not a person, you're just a sissy fuck toy (a girl on all fours taking a cock in both her mouth and her pussy, bouncing back and forth like a manic rocking horse).

It's weird... really weird... that my physical response to that statement was my cock flinching in my panties (equally weird that I could even accurately speak of 'my panties').

Yet the idea of my being a fuck toy for two cocks (not two men, men didn't turn me on, but hard cocks were just so visually appealing) was stirring inside me.

God, when I'm horny, my mind goes places I never thought it would before this entire adventure began:

Crossdressing.

Sucking cock.

Even taking it in the ass.

Fuck!

#76: Sissies love bukkake (a girl with a few loads dribbling down all over her face).

Again, the idea of a facial was hot... the idea of cock after cock spewing on my face was captivatingly intriguing.

Fuck!

#116: Sissies don't fuck women, women fuck sissies (a gif of a hot woman wearing a strap-on continuously fucking a guy in the ass).

Fuck, that's hot!

Although the idea of a guy fucking me was somewhat intriguing, the truth was, it scared me and seemed very gay (somehow sucking a cock didn't... not that I'm making any sense).

On the other hand, the idea of a woman fucking me with a strap-on seemed hot as fuck. I mean if Deadpool can take it in the ass, I sure as hell could (I know I've already said that earlier, but it seemed like a fair rationale).

Again, I wondered whether Paige would don a strap-on for me.

Would she be willing to fuck me hard like this woman was doing to her guy?

Fuck!

#143: No cock is too big for a sissy like you (a huge cock spreading a cheerleader's ass).

Since the idea of sucking a cock was growing in me, and since the idea of being sodomized was lingering, the issue of size was becoming pertinent.

Too long would make me gag.

Too thick would tear my ass apart. Why am I even going there? Fuck!

Yet I would be lying if I pretended I wasn't fascinated by big cocks. I mean truthfully, I was fascinated by all cocks, but long cocks and thick dicks really drew me in.

Just like girls with average sized breasts (as I have an average sized tool), you always want what you don't have.

#164 A sissy must be a perfect submissive. On her knees with her mouth open is not only where she belongs, it's where she lives (a girl in a nurse's outfit on her knees with a nice cock in her mouth).

I realized the themes were beginning to get repetitive, as if repeated concepts could condition me properly. As I stared at the cock and not at the girl, I began to think that idea may be true, including in my own case.

#173 A sissy must learn not just to love cock, but to worship cock (a redhead kneeling on a bed stroking two black men with large chocolate cocks).

I just called a cock chocolate. As in something delicious and habit-forming,

I wonder what it would feel like to be stroking those massive BBC's.

I wonder what it would be like to suck one.

I wonder what it would be like to have one in my ass.

I wonder what it would be like to have one pummelling me in each end.

Fuck!

#181 Sissies have no need to worry their pretty little heads with big words or complex thoughts. Sissies are blissfully dumb. All they think about is cock (A blonde-haired girl moving back and forth from one big cock to another).

I couldn't fathom this one. I was an academic. Yet even so, I could still tell I was being manipulated by the pictures, the gifs and the words. Even analyzing the logic of how it worked didn't diminish its effect on me.

I wasn't being brainwashed per se... but I could feel the psychological seeds being planted and taking root.

#183 A sissy is always on her knees ready and waiting before his cock even comes out (a gif, one of the best ever, of a short blonde on her knees literally bouncing up and down with excitement as a sitting man fishes out his cock).

I wonder what I would feel if this fantasy became real.

What if I were on my knees in front of a cock?

What would I feel?

Hunger?

Eagerness?

Lust?

Fuck!

#198 Don't think of begging on your knees as being degrading (a brunette in stockings on her knees in front of a black man with a cock so huge that I imagine almost any woman would beg to have it).

I imagine if you'd made the commitment to lower yourself before a cock... begging would be the natural next step.

#201 Before you pleasure a man's cock, take a moment to admire its beautiful size and shape. Take it all in with your eyes before you take it all into your mouth (a woman on her knees, a constant in these pictures and gifs, staring at a cock with lustful admiration).

This was how it started for me.

I started noticing the different cocks.

Different lengths.

Different shapes.

Different girths.

Different colours.

I hadn't realized I was doing it, but for the past few months I'd been admiring cocks, and not just since Christmas.

#227 When you wear a butt plug, don't think of it as a toy. Think of it as a place holder for the next big cock you'll have the pleasure of being filled up with. Let this surrogate cock motivate you to find a man who will replace it with his living cock (a young-looking girl with a ponytail lifting up her short skirt to display a plug in her ass)

This one really amused me.

I couldn't explain it.

But the words, although ludicrous, made perfect sense to me.

By now I desperately needed to come.

So I tried to calm myself down, feeling compelled to obey my Mistress and to refrain from coming.

I decided to send the pictures and gifs I'd chosen so far to Mistress M. To my surprise, I counted 29 pictures that I'd saved, more than double the required number.

I shrugged, zipped all the pictures and sent them off with a brief note:

Sorry, I couldn't limit them to 12.

Kendra

I sent it and then shook my head at signing it Kendra without even a thought.

Wanting a break from my raging rod, I found the YouTube clip about high heels and pressed Play.

The clip began with a very attractive and personable black lady introducing herself and then saying, "I'm here to show you the right way to strut your stuff in heels."

I was hoping simply not to die in heels.

The lady suggested beginning with wedge heels for super stability... a style which I didn't have.

She followed with chunky heels... which I also didn't have. Mine were stilettos.

She called the stiletto the mother of all heels... and I had to agree with her.

Mine had platforms at the front below my toes, just like in the video. She stressed that these give you the ultimate effect, and they're easy to walk in so long as you properly concentrate your weight on your heels or your toes in varying conditions.